(6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 39685-31-9
• Molecular Formula: C17H17N3O8S
• Molecular Weight: 423.403
• European Community (EC) Number: 254-592-2
• UNII: 9FA4SWZ5ZT
• DSSTox Substance ID: DTXSID101100961
• Nikkaji Number: J91.947K
• Wikidata: Q27277711
• Mol file: 39685-31-9.mol

Synonyms:97232-98-9;Cefuracetime (E-isomer);9FA4SWZ5ZT;SKF81367;UNII-9FA4SWZ5ZT;(6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefuroxime sodium impurity G [EP];39685-31-9;(6R,7R)-3-((Acetyloxy)methyl)-7-(((E)-(furan-2-yl)(methoxyimino)acetyl)amino)-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid;5-Thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 3-((acetyloxy)methyl)-7-((2-furanyl(methoxyimino)acetyl)amino)-8-oxo-, (6R-(6alpha,7beta(E)))-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-, [6R-[6alpha,7beta(E)]]-;SCHEMBL615048;YBHZVPYSEUQIII-MKHSIZEZSA-N;DTXSID101100961;A900172;CEFUROXIME SODIUM IMPURITY G [EP IMPURITY];Q27277711;7-[2-(2-Furyl)-2-methoxyiminoacetamido]cephalosporanic acid;5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-7-((2-FURANYL(METHOXYIMINO)ACETYL)AMINO)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(E)))-

Chemical Property of (6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

• Melting Point: >124°C (dec.)
• Boiling Point: °Cat760mmHg
• PKA: 2.66±0.50(Predicted)
• Flash Point: °C
• PSA: 176.53000
• Density: 1.63g/cm³
• LogP: 0.71000
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 8
• Exact Mass: 423.07363568
• Heavy Atom Count: 29
• Complexity: 796

Purity/Quality:

98%Min ^*data from raw suppliers

Cefuracetime ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1=C(N2C(C(C2=O)NC(=O)C(=NOC)C3=CC=CO3)SC1)C(=O)O
• Isomeric SMILES: CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N/OC)/C3=CC=CO3)SC1)C(=O)O
• Uses: Cefuracetime is an impurity of Cefuroxime, which is an antibacterial.

Technology Process of (6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 3 articles about (6R,7R)-3-(acetyloxymethyl)-7-[[(2E)-2-(furan-2-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

furan-2-yl-oxo-acetaldehyde (17090-71-0) + O-Methylhydroxylamin (67-62-9) + 7-Aminocephalosporanic acid (957-68-6) → 7-[(Z)-2-Furyl-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephalosporanic acid (39685-31-9)

Guidance literature:

furan-2-yl-oxo-acetaldehyde; 7-Aminocephalosporanic acid; With tert.-butylhydroperoxide; C₈H₁₉Cl₂OPPd; In 2-methyltetrahydrofuran; at 45 ℃; for 2.5h; Sealed tube; Inert atmosphere;

O-Methylhydroxylamin; With Trimethylacetic acid; In 2-methyltetrahydrofuran; water; at 45 ℃; for 2.5h; Reagent/catalyst; Solvent; Temperature; Sealed tube; Inert atmosphere;

Reference yield:

(2Z)-2-furyl(methoxyimino)acetyl-p-toluenesulfonic anhydride + 7-Aminocephalosporanic acid (957-68-6) → 7-[(Z)-2-Furyl-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephalosporanic acid (39685-31-9)

Guidance literature:

7-Aminocephalosporanic acid; With triethylamine; In chloroform; for 0.5h;

(2Z)-2-furyl(methoxyimino)acetyl-p-toluenesulfonic anhydride; In chloroform; at 0 - 5 ℃; for 2h;

Reference yield:

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt (97148-39-5) → 7-[(Z)-2-Furyl-2-methoxyiminoacetamido]-3-acetoxymethyl-3-cephalosporanic acid (39685-31-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / chloroform / 0.17 h / 5 °C

1.2: 1 h

2.1: triethylamine; chloro-trimethyl-silane / chloroform / 0.5 h / 5 °C

2.2: 4 h / 5 °C

With chloro-trimethyl-silane; triethylamine; In chloroform;

upstream raw materials:

7-Aminocephalosporanic acid

(Z)-2-methoxyimino-2-(furyl-2-yl)acetic acid ammonium salt

furan-2-yl-oxo-acetaldehyde

O-Methylhydroxylamin

Downstream raw materials:

(6R,7R)-7-[2-(2-furyl)-2-(methoxyimino)acetamido]-3-hydroxymethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Cefuroxime

Refernces

• 1、 -. "Cefuroxime sodium compound prepared through advanced on-line process control technology and preparation thereof". Paragraph 0038; 0048; 0076. . Retrieved 2017/02/28.