2-(2-Aminothiazol-4-yl)glyoxylic acid

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2-(2-Aminothiazol-4-yl)glyoxylic acid Basic information
Product Name:2-(2-Aminothiazol-4-yl)glyoxylic acid
Synonyms:2-(2-AMINOTHIAZOL-4-YL) GLYOXYLIC ACID;2-(2-AMINOTHIAZOL-4-YL)-2-OXO-ACETIC ACID;2-amino-α-oxothiazol-4-acetic acid;2-amino-alpha-oxothiazol-4-acetic acid;ATGA:2-(2-AMINOTHIAZOL-4-YL) GLYOXYLIC ACID;2-(2-aminothiazol-4-yl)glyoxylic Acid (ATGA);ATGA;2-Amino-4-thiazoleglyoxylic Acid
CAS:73150-67-1
MF:C5H4N2O3S
MW:172.16
EINECS:277-301-0
Product Categories:Organic acids
Mol File:73150-67-1.mol
2-(2-Aminothiazol-4-yl)glyoxylic acid Structure
2-(2-Aminothiazol-4-yl)glyoxylic acid Chemical Properties
Boiling point 395.7±24.0 °C(Predicted)
density 1.711±0.06 g/cm3(Predicted)
storage temp. 2-8°C(protect from light)
solubility DMSO
form Solid
pka1.25±0.54(Predicted)
color Pale Yellow
InChIInChI=1S/C5H4N2O3S/c6-5-7-2(1-11-5)3(8)4(9)10/h1H,(H2,6,7)(H,9,10)
InChIKeyVMASTYPGLHRVNL-UHFFFAOYSA-N
SMILESC1(C(=O)C(=O)O)N=C(N)SC=1
CAS DataBase Reference73150-67-1(CAS DataBase Reference)
Safety Information
MSDS Information
2-(2-Aminothiazol-4-yl)glyoxylic acid Usage And Synthesis
Uses2-Amino-4-thiazoleglyoxylic Acid is an intermediate in synthesizing (6R,7R)-7-(2-(2-Aminothiazol-4-yl)-2-oxoacetamido)-8-oxo-3-vinyl-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid (A630310), which is used in the preparation of Cephalosporin C (C258750), an antibiotic used to study the effect of transpeptidase expression, binding, and inhibition on bacterial cell wall mucopeptide synthesis.
Synthesis
4-Thiazoleethanethioic acid, 2-amino-α-oxo-, S-methyl ester

89721-50-6

2-(2-Aminothiazol-4-yl)glyoxylic acid

73150-67-1

Under ice bath cooling conditions, 10.1 g of methyl 2-(2-aminothiazol-4-yl)thioacetoxy S-acid (CAS: 89721-50-6) was mixed with 80 mL of water, followed by the addition of 10.6 g of sodium carbonate. The reaction mixture was stirred continuously for 1 h at a maintained ice bath temperature. Upon completion of the reaction, the pH of the reaction mixture was adjusted to 2.5 at the same temperature using 6 N hydrochloric acid. the precipitated crystals were collected by filtration, washed with deionized water and subsequently dried to afford 6.2 g (67.8% yield) of 2-(2-aminothiazol-4-yl)glyoxalic acid with a melting point of more than 200°C. The infrared spectra of the product (KBr pressed slice) showed a νC=O absorption peak at 1660 cm1.

References[1] Patent: US4563534, 1986, A
2-(2-Aminothiazol-4-yl)glyoxylic acid Preparation Products And Raw materials
Raw materials4-Thiazoleethanethioic acid, 2-amino-α-oxo-, S-methyl ester-->Water-->Sodium carbonate
Tag:2-(2-Aminothiazol-4-yl)glyoxylic acid(73150-67-1) Related Product Information
Glyoxylic acid Lithium bis(trimethylsilyl)amide Ethyl glyoxalate SODIUM GLYOXYLATE Molasses Sodium N-cyclohexylsulfamate Thiazole 2-Aminothiazole (2-Formamido-1,3-thiazol-4-yl)glyoxylic acid ETHYL 2-(2-FORMYLAMINO-1,3-THIAZOL-4-YL)-2-OXOACETATE Ethyl 2-(2-aminothiazol-4-yl)glyoxylate 2-AMINO-5-(BROMOTHIAZOL-4-YL)OXOACETIC ACID METHYL ESTER ETHYL 2-(2-[(4-CHLOROBENZOYL)AMINO]-1,3-THIAZOL-4-YL)-2-OXOACETATE 2-(2-Aminothiazol-4-yl)glyoxylic acid