24701-69-7

Basic information

• Product Name: 7-AMCA
• Synonyms: 7-AMINO-3-METHOXYMETHYL-3-CEPHEM-4-CARBOXYLIC ACID;7-amino 3-methyloxymethyl-3-cephem 4-carboxylic acid;7-AMCA;7-Amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;7-AMINO 3-METHYLOXYMETHYL-3-CEPHEM 4-CARBOXYLIC AICD;7-AMino-3-MethoxyMethyl-3-cepheM-4-carboxylicacid (7-AMCA);(6R,7R)-7-AMino-3-(MethoxyMethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;24701-69-1
• CAS NO: 24701-69-7
• Molecular Formula: C₉H₁₂N₂O₄S
• Molecular Weight: 244.27
• EINECS: 1592732-453-0
• Product Categories: Amines
• Mol File: 24701-69-7.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 519.401 °C at 760 mmHg
• Flash Point: 267.924 °C
• Appearance: /
• Density: 1.55
• Vapor Pressure: 7.72E-12mmHg at 25°C
• Refractive Index: 1.663
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2.70±0.50(Predicted)
• Water Solubility: 87.7mg/L at 20℃
• CAS DataBase Reference: 7-AMCA(CAS DataBase Reference)
• NIST Chemistry Reference: 7-AMCA(24701-69-7)
• EPA Substance Registry System: 7-AMCA(24701-69-7)

Safety Data

• Hazardous Substances Data: 24701-69-7(Hazardous Substances Data)

Usage

Description

7-Amino-3-(methoxymethyl)-3-cephem-4-carboxylic Acid, commonly known as 7-AMCA, is a chemical compound that serves as a key reactant in the pharmaceutical industry. It is primarily used in the synthesis of prodrug-type cephalosporins, which are a class of antibiotics known for their broad-spectrum antimicrobial properties.

Uses

Used in Pharmaceutical Industry:
7-AMCA is used as a reactant for the preparation of prodrug-type cephalosporins for the following reasons:
1. It plays a crucial role in the synthesis of these antibiotics, which are essential in treating a wide range of bacterial infections.
2. The use of 7-AMCA in the production process allows for the development of cephalosporins with improved pharmacokinetic properties, such as better absorption, distribution, and excretion in the body.
3. By incorporating 7-AMCA into the synthesis, prodrug-type cephalosporins can be designed to have enhanced stability, reduced side effects, and increased effectiveness against resistant bacterial strains.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H12N2O4S/c1-15-3-4-2-11-7(12)5(10)8(11)16-6(4)9(13)14/h5,8H,2-3,10H2,1H3,(H,13,14)/t5?,8-/m0/s1

Synthetic route

(6R,7R)-7-Amino-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (R)-1-(2,2-dimethyl-propionyloxy)-ethyl ester; hydrochloride → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With sodium hydroxide In methanol at 25 - 30℃; for 5h; immobilized enzyme, pH 6.8;	81%

Trimethyl borate (121-43-7) + methyl bisulfate (75-93-4) + 7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
In methanol; N,N-dimethyl-formamide at 0 - 20℃; for 5h;	66.88%

methanol (67-56-1) + 7-Aminocephalosporanic acid (957-68-6) → 6t-amino-(5ar)-5a,6-dihydro-3H,4H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7-dione (184696-69-3) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid; trifluorormethanesulfonic acid at 13 - 14℃; for 0.75h; Yield given. Yields of byproduct given;

7-Aminocephalosporanic acid (957-68-6) → 6t-amino-(5ar)-5a,6-dihydro-3H,4H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7-dione (184696-69-3) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid; trifluorormethanesulfonic acid In methanol at 13 - 14℃; for 0.75h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

methanol (67-56-1) + 7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
Stage #1: methanol; 7-Aminocephalosporanic acid; boron trifluoride In sulfolane Stage #2: With triethylamine In sulfolane; methanol; water
With methanesulfonic acid at 5 - 12℃; Reagent/catalyst; Temperature;

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) + trimethyl orthoformate (149-73-5) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid In acetonitrile at 5 - 40℃; Reagent/catalyst; Solvent;
Stage #1: trimethyl orthoformate With boron trifluoride diethyl etherate In acetonitrile at -20 - 25℃; for 0.916667h; Stage #2: (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid In acetonitrile at 25℃; Temperature;

Trimethyl borate (121-43-7) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid at 5 - 40℃;

(6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) + dimethyl sulfate (77-78-1) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid at 5 - 40℃;

Methyl formate (107-31-3) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid at 5 - 40℃;

Dimethoxymethane (109-87-5) + (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (15690-38-7) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
With methanesulfonic acid at 5 - 40℃;

Trimethyl borate (121-43-7) + 7-Aminocephalosporanic acid (957-68-6) → (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7)

Conditions	Yield
Stage #1: 7-Aminocephalosporanic acid With 1H-imidazole; 1,1,1,3,3,3-hexamethyl-disilazane In dimethyl sulfoxide at 30 - 35℃; for 1h; Inert atmosphere; Stage #2: Trimethyl borate With methanesulfonic acid In methanol; dimethyl sulfoxide at 0 - 5℃; Concentration; Solvent; Reagent/catalyst;	43 g

(Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate (80756-85-0) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Conditions	Yield
With triethylamine In tetrahydrofuran at -5 - 5℃; for 2h;	82.86%
Stage #1: (Z)-S-benzo[d]thiazol-2-yl 2-(2-aminothiazol-4-yl)-2-(methoxyimino)ethanethioate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In methanol at 8 - 12℃; Stage #2: With sulfuric acid In methanol; water at 0 - 20℃; pH=2.4 - 2.5; Product distribution / selectivity;
With triethylamine In methanol; water at 15 - 20℃;	81 mg

C13H7(2)H3N4O2S3 + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime-d3

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 20℃; for 2h; Cooling with ice;	69%

1-iodoethyl 2,2-dimethylpropionate (80195-78-4) + C35H33N3O6S2 (77934-90-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefdaloxime + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(E)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

1-iodoethyl 2,2-dimethylpropionate (80195-78-4) + C35H33N3O6S2 (77934-90-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → 2,2-Dimethyl-propionic acid 1-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetoxy}-ethyl ester + (6R,7R)-7-{2-[(Z)-Hydroxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-3-Methoxymethyl-7-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-3-Methoxymethyl-7-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine 1.) CH2Cl2, 15 deg C, 30 min; acetone, 0-5 deg C, 30 min, 2.) acetone, 20 deg C, 10 min; 20 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine 1.) CH2Cl2, 15 deg C, 30 min; acetone, 0-5 deg C, 30 min, 2.) acetone, 20 deg C, 10 min; 20 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

C35H33N3O6S2 (77934-90-8) + 2,2-dimethyl-propionic acid (RS)-1-bromo-ethyl ester (55419-51-7) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → (6R,7R)-3-Methoxymethyl-7-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-3-Methoxymethyl-7-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine 1.) CH2Cl2, 15 deg C, 30 min; acetone, 0-5 deg C, 30 min, 2.) acetone, 20 deg C, 27 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;
With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine 1.) CH2Cl2, 15 deg C, 30 min; acetone, 0-5 deg C, 30 min, 2.) acetone, 20 deg C, 27 h; Yield given. Multistep reaction. Yields of byproduct given;

C35H33N3O6S2 (77934-90-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefdaloxime + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-7-{2-(2-Amino-thiazol-4-yl)-2-[(E)-hydroxyimino]-acetylamino}-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions	Yield
Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts;

C35H33N3O6S2 (77934-90-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → (6R,7R)-3-Methoxymethyl-7-{2-[(Z)-1-methoxy-1-methyl-ethoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid + [(Z)-1-Methoxy-1-methyl-ethoxyimino]-[2-(trityl-amino)-thiazol-4-yl]-acetic acid; compound with triethyl-amine + (Z)-2-Hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)-acetic acid (68672-45-7)

Conditions	Yield
With triethylamine 1.) CH2Cl2, 15 deg C, 30 min, 2.) acetone, 0-5 deg C, 30 min; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

2,2-dimethyl-propionic acid (RS)-1-bromo-ethyl ester (55419-51-7) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → (6R,7R)-7-Amino-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (S)-1-(2,2-dimethyl-propionyloxy)-ethyl ester + (6R,7R)-7-Amino-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (R)-1-(2,2-dimethyl-propionyloxy)-ethyl ester

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone 1.) r.t., 15 min, 2.) r.t., 4 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone 1.) r.t., 15 min, 2.) r.t., 4 h; Yield given. Yields of byproduct given;

chloro-trimethyl-silane (75-77-4) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → C15H28N2O4SSi2

Conditions	Yield
With 1,1,1,3,3,3-hexamethyl-disilazane In dichloromethane for 3h; Heating;

(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → 7-[2-(2,8-bis-trifluoromethyl-quinolin-4-yloxy)-propionylamino]-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,1,1,3,3,3-hexamethyldisilazane / CH2Cl2 / 3 h / Heating 2: 28 percent / CH2Cl2 / 2 h / -25 - -20 °C View Scheme

(6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → (6R,7R)-7-[2-(2,8-Bis-trifluoromethyl-quinolin-4-yloxy)-acetylamino]-3-methoxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Conditions	Yield
Multi-step reaction with 2 steps 1: 1,1,1,3,3,3-hexamethyldisilazane / CH2Cl2 / 3 h / Heating 2: 64 percent / CH2Cl2 / 2 h / -25 - -20 °C View Scheme

2-(2-aminothiazol-4-yl)-2(Z)-(methoxyimino)mercaptobenzothiazolyl acetate + 1-iodoethyl isopropyl carbonate (84089-73-6, 91508-00-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → vantin

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; ethyl acetate

1-iodoethyl isopropyl carbonate (84089-73-6, 91508-00-8) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → 1-(Isopropoxycarbonyloxy)ethyl (6R,7R)-7-amino-3-methoxymethyl-3-cephem-4-carboxylate p-toluenesulfonate (148893-80-5)

Conditions	Yield
With p-toluenesulfonic acid monohydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane; di-isopropyl ether; ethyl acetate

(benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Conditions	Yield
Stage #1: (benzothiazol-2-yl)-2-(2-aminothiazol-4-yl)-Z-2-methoxyimino-thioacetate; (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid With triethylamine In methanol; water at 15 - 20℃; Stage #2: With sulfuric acid In methanol; water

2-(2-amino-1,3-thiazol-4-yl)-1-(1,3-benzothiazol-2-ylsulfanyl)-2-(methoxyimino)ethan-1-one (94088-75-2) + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Conditions	Yield
With triethylamine In dichloromethane at 5 - 25℃; pH=8 - 9; Temperature;

C12H14N6O5S2 + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → C21H22N8O8S3

Conditions	Yield
With triethylamine In tetrahydrofuran; dichloromethane at 20 - 25℃; for 5h;	16.2 g

C13H13N3O5S2 + (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (24701-69-7) → cefpodoxime (80210-62-4)

Conditions	Yield
With triethylamine In methanol at -30 - 0℃; for 0.5h; Solvent;

Upstream product

• 121-43-7 Trimethyl borate 
• 957-68-6 7-Aminocephalosporanic acid 
• 109-87-5 Dimethoxymethane 
• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 107-31-3 Methyl formate 
• 77-78-1 dimethyl sulfate 
• 149-73-5 trimethyl orthoformate 
• 75-93-4 methyl bisulfate 
• 67-56-1 methanol 

Downstream Products

• 80210-62-4 cefpodoxime 
• 87239-81-4 cefpodoxime proxetil 
• 148893-80-5 1-(Isopropoxycarbonyloxy)ethyl (6R,7R)-7-amino-3-methoxymethyl-3-cephem-4-carboxylate p-toluenesulfonate 
• 68672-45-7 (Z)-2-Hydroxyimino-2-(2-triphenylmethylaminothiazol-4-yl)-acetic acid 
• 80195-36-4 cefdaloxime 

Relevant articles and documents

Preparation method of cefpodoxime acid

The invention discloses a preparation method of cefpodoxime acid. The method comprises the following steps: adding a proper amount of solvent, 7-amino-3-chloromethyl cephalosporanic acid as shown in a formula (III), sodium methoxide, a quaternary ammonium salt catalyst and potassium iodide into a reaction container, performing stirring reaction at 0-80 DEG C for 2-8 hours, then adding 2-(2-amino-4-thiazolyl)-2-(Z)-methoxy imino acetyl chloride as shown in a formula (IV), performing stirring reaction at 0-30 DEG C for 2-5 hours, and after the reaction is finished, performing post-treatment to obtain cefpodoxime acid as shown in a formula (II). The method is simple and easy to operate, high in reaction yield, green and environmentally friendly, avoids the use of inflammable and explosive raw materials with high toxicity, improves the purity of the product by the post-treatment process, and is suitable for industrial production.

Preparation method of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid

The invention discloses a preparation method of 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid, and relates to the technical field of preparation of pharmaceutical intermediates. The method includes the steps that under the protection of nitrogen, 7-aminocephalosporanic acid, a silane reagent and an imidazole catalyst are stirred for 0.5-2 h at 30-35 DEG C in a water-soluble organic solvent; then, the mixture is cooled to 0-5 DEG C, methanesulfonic acid, trimethyl borate and methyl alcohol are added, a methoxylation reaction is conducted with the temperature controlled to be 0-5 DEG C, and 7-amino-3-methoxymethyl-3-cephem-4-carboxylic acid is obtained, wherein the silane reagent is hexamethyldisilazane or trimethylchlorosilane or N,O-bis(trimethylsilyl)acetamide or dimethoxydimethylsilane. According to the method, the product purity is high, the impurity content is low, operation is easy and convenient, refining steps are simplified, production cost is reduced, and the method is suitable for industrial production.

Synthesis method of cefpodoxime proxetil intermediate

The invention discloses a synthesis method of a cefpodoxime proxetil intermediate, namely (6R,7R)-7-[2-(2-amino-4-thiazolyl)-(Z)-2-(methoxyimino)acetamido]-3-methoxymethyl-8-oxo-5-thio-1-azabicyclo[4.2.0]oct-2-ene-2-methanoic acid. The synthesis method includes: enabling chlorosulfonic acid and methanol to react to prepare methoxy sulfonic acid; under the action of the methoxy sulfonic acid and dimethylformamide, etherifying 7-ACA (7-aminocephalosporanic acid) and trimethyl borate prior to aftertreatment, adding into a water and methanol solution reversely to guarantee that the obtained intermediate isn't sticky and is loose, drying and grafting with AE active ester so as to obtain a target product, namely the cefpodoxime proxetil intermediate. The synthesis method of the cefpodoxime proxetil intermediate has the advantages that synthesis steps of 3-position and 7-position protection and desorption of 7-ACA can be omitted, so that low step cost, high yield and high purity are achieved, all materials are cheap and available, and industrial production and little pollution are benefited.