72217-12-0

Basic information

• Product Name: 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid
• Synonyms: 2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-(METHOXYIMINO)ACETIC ACID;(5-AMINO-[1,2,4]THIADIAZOL-3-YL)-METHOXYIMINO-ACETIC ACID;ATDA:( Z ) -2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID;2-（5-amino-1,2,4-thiadiazol-3-yl） 2-(Z)-methoxyimino acetic acid;2-METHOXYIMINO-2-(5-ANMINO-1,2,4-THIADIAZOL-3-YL)ACETIC ACID;(Z) -2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino acetic;2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid ,98%;2-(5-Boc-Amino-1,2,4-thiadiazol-3-yl)-2-methoxyimino acetic acid
• CAS NO: 72217-12-0
• Molecular Formula: C₅H₆N₄O₃S
• Molecular Weight: 202.19
• EINECS: 1806241-263-5
• Product Categories: pharmacetical;Organic acids
• Mol File: 72217-12-0.mol

Chemical Properties

• Boiling Point: 430.4 °C at 760 mmHg
• Flash Point: 214.1 °C
• Appearance: /
• Density: 1.83
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.749
• Storage Temp.: 2-8°C(protect from light)
• PKA: 2.46±0.41(Predicted)
• CAS DataBase Reference: 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid(72217-12-0)
• EPA Substance Registry System: 2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid(72217-12-0)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• Hazardous Substances Data: 72217-12-0(Hazardous Substances Data)

Usage

Chemical Properties

White solid

InChI:InChI=1/C5H6N4O3S/c1-12-8-2(4(10)11)3-7-5(6)13-9-3/h1H3,(H,10,11)(H2,6,7,9)/b8-2-

Upstream product

• 149196-73-6 methyl (Z)-2-(5-methoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetate 
• 84981-73-7 2-(5-amino-1,2,4-thiadiazol-3-yl)-(Z)-2-methoxyiminoacetonitrile 
• 149196-78-1 ethyl 2-(5-ethoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetate 
• 111-42-2 2,2'-iminobis[ethanol] 

Downstream Products

• 153163-95-2 (6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-(benzothiazol-2-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 153164-00-2 (6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-3-(thiazolo[5,4-b]pyridin-2-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 144581-74-8 (6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 105240-03-7 (6R,7R)-7-{2-(5-Amino-[1,2,4]thiadiazol-3-yl)-2-[(Z)-methoxyimino]-acetylamino}-3-iodomethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 89604-91-1 (Z)-(5-amino-[1,2,4]thiadiazol-3-yl)methoxyiminothioacetic acid S-benzothiazol-2-yl ester 

Relevant articles and documents

Process for preparing 1,2,4-thiadiazole derivatives

An improved process for the production of 5-amino-1,2,4-thiadiazol-3-yl-(2-(lower)-alkoxyimino)acetic acids starting from 5-substituted- or unsubstituted-3-amino-isoxazole compounds is disclosed herein. The title compounds are useful as acylating agents for the production of 7-acylaminocephalosporins.

Practical preparation of (Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetic acid: A side-chain of the fourth generation of cephem antibiotics

A Z-isomer (4) of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid, which is the common acyl moiety of clinically useful cephem antibiotics, has been prepared from the aminoisoxazoles through the skeletal rearrangement in several routes. Reaction of 3-amino-5-methoxyisoxazole (7) with alkoxycarbonyl isothiocyanates gave methyl 2-(5-alkoxycarbonylamino-1,2,4-thiadiazol-3-yl)acetates (8), which were converted into the target compound 4 through the reaction of the corresponding keto ester with O-methylhydroxylamime. Compound 4 was prepared similarly from 3-aminoisoxazole (10). Also, O-methylation of 2-hydroxyimino-2-(5-methoxycarbonylamino-1,2,4-thiazol-3-yl)acetate (15) with methyl iodide or dimethyl sulfate in the presence of barium oxide and barium hydroxide octahydrate was found to afford exclusively the desired Z-isomer (14a) of methyl 2-(5-methoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)aceta te, which was led to 4.

A Practical Preparation of (Z)-2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic Acid

A Z-isomer of 2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(methoxyimino)acetic acid, which is the common acyl moiety of clinically useful cephalosporins, has been prepared from the aminoisoxazols through the thiadiazol-acetate in two pathways.

Cephalosporin derivatives

7-[2-(5-Amino-1,2,4-thiadiazol-3-yl)-2-(substituted)-iminoacetamido]-3-[3-(quaternaryammonio)-1-propen-1-yl]-3-cephem-4-carboxylates of the formula STR1 in which R1 and R2 are defined herein and --≈ N Q is a quaternary ammonio group as defined herein, and salts, solvates, hydrates and esters thereof, are potent antibacterial agents. Processes for their preparation and intermediates in such processes are described.