68786-47-0

Basic information

• Product Name: (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID
• Synonyms: ATDA;(Z)-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOACETIC ACID;(Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID;TTOA;( Z )-2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOACETIC ACID (TTOA);TTOA:( Z ) -2-(2-TRITYLAMINOTHIAZOL-4-YL)-2-TRITYLOXYIMINOACETIC ACID
• CAS NO: 68786-47-0
• Molecular Formula: C₄₃H₃₃N₃O₃S
• Molecular Weight: 202.19
• Mol File: 68786-47-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 832.8°C at 760 mmHg
• Flash Point: 457.5°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 2.08E-29mmHg at 25°C
• Refractive Index: 1.643
• CAS DataBase Reference: (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID(68786-47-0)
• EPA Substance Registry System: (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID(68786-47-0)

Safety Data

• Hazardous Substances Data: 68786-47-0(Hazardous Substances Data)

Usage

Uses

Intermediate in the preparation of Cefdinir (C242670).

InChI:InChI=1/C43H33N3O3S/c47-40(48)39(46-49-43(35-25-13-4-14-26-35,36-27-15-5-16-28-36)37-29-17-6-18-30-37)38-31-50-41(44-38)45-42(32-19-7-1-8-20-32,33-21-9-2-10-22-33)34-23-11-3-12-24-34/h1-31H,(H,44,45)(H,47,48)/b46-39+

Upstream product

• 76-83-5 trityl chloride 
• 66338-96-3 2-(2-Amino-1,3-thiazol-4-yl)-2-(hydroxyimino)acetic acid 
• 69689-86-7 ethyl 2-(2-tritylaminothiazol-4-yl)-(Z)-2-(tritylhydroxyimino)acetate 
• 64485-82-1 (Z)-ethyl 2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate 
• 128438-01-7 (Z)-2-(2-aminothiazol-4-yl)-2-(triphenylmethoxyimino)acetic acid 

Downstream Products

• 162704-75-8 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-iodomethyl-3-cephem-4-carboxylate 
• 133731-50-7 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-hydroxy-1-propenyl>-3-cephem-4-carboxylate 
• 133731-36-9 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-(N-methylcarbamoyloxy)-1-propenyl>-3-cephem-4-carboxylate 
• 133731-54-1 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-(N-ethylcarbamoyloxy)-1-propenyl>-3-cephem-4-carboxylate 
• 133754-57-1 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-(N,N-dimethylcarbamoyloxy)-1-propenyl>-3-cephem-4-carboxylate 
• 133731-53-0 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-(N-isopropylcarbamoyloxy)-1-propenyl>-3-cephem-4-carboxylate 
• 133731-49-4 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-tert-butyldimethylsilyloxy-1-propenyl>-3-cephem-4-carboxylate 
• 160786-22-1 (6R,7R)-8-Oxo-3-[(Z)-3-(pyrrolidine-1-carbonyloxy)-propenyl]-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 133731-55-2 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-(N-allylcarbamoyloxy)-1-propenyl>-3-cephem-4-carboxylate 
• 133731-63-2 (6R,7R)-3-[(Z)-3-(Morpholine-4-carbonyloxy)-propenyl]-8-oxo-7-{2-[2-(trityl-amino)-thiazol-4-yl]-2-[(Z)-trityloxyimino]-acetylamino}-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 133731-33-6 4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-trityloxyiminoacetamido>-3-<(Z)-3-carbamoyloxy-1-propenyl>-3-cephem-4-carboxylate 
• 153502-35-3 (7S,6R)-7-<<(2-amino-4-thiazolyl)hydroximinoacetyl>amino>-3-chloro-1-carba-1-dethia-3-cephem-4-carboxylic acid 
• 153502-34-2 (7S,6R)-7-<<2-<(tritylamino)-4-thiazolyl>trityloximinoacetyl>amino>-3-chloro-1-carba-1-dethia-3-cephem-4-carboxylic acid 
• 153502-33-1 (7S,6R)-7-<<2-<(tritylamino)-4-thiazolyl>trityloximinoacetyl>amino>-3-chloro-3-cephem-4-carboxylic acid 

Relevant articles and documents

CARBACEPHEM β-LACTAM ANTIBIOTICS

Carbacephem -lactam antibiotics having structure (I) are disclosed, including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar1, Ar2, R1 and R2 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

CARBACEPHEM BETA-LACTAM ANTIBIOTICS

Carbacephem β-lactam antibiotics having chemical structures (I) and (II) are disclosed: including stereoisomers, pharmaceutically acceptable salts, esters and prodrugs thereof, wherein Ar2, R1, R2 and R6 are as defined herein. The compounds are useful for the treatment of bacterial infections, in particular those caused by methicillin-resistant Staphylococcus spp.

Synthesis of HR 916 K: An efficient route to the pure diastereomers of the 1-(pivaloyloxy)ethyl esters of cephalosporins

HR 916 K (5), the 1-(S)-(pivaloyloxy)ethyl prodrug ester of the cephalosporin cefdaloxime, exhibits a significantly higher oral bioavailability than the 1-(R) diastereomer HR 916 J. An efficient synthesis of HR 916 K was developed. The separation of the diastereomers was achieved by precipitation of the 1-(R)-hydrochloride 9 followed by crystallization of the 1-(S)-amine 10 (de > 96%). The 1-(R) diastereomer 9 was recycled by acidic saponification or enzymatic cleavage to AMCA (7). The amine 10 was acylated with mercaptobenzothiazole thioesters or mixed anhydrides, prepared from carboxylic acids 13 and 14, in almost quantitative yield. Deprotection of the oxime and formation of the tosylate proceeded in one step. Using thioester 18, we obtained HR 916 K (5) from AMCA (7) in 42% yield. VCH Verlagsgesellschaft mbH, 1996.