89604-92-2

Basic information

• Product Name: 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate
• Synonyms: 2-MERCAPTOBENZOTHIAZOLYL-(Z)(2-AMINOTHIAZOLE-4YL)-2-(TERT-BUTOXYCARBONYL)ISOPROPOXYIMINO ACETATE;S-2-BENZOTHIAZOYL-(Z)-2-(1-TERT-BUTOXYCARBONYL-1-METHYLETHOXYIMINO)-2-(AMINOTHIAZOL-4-YL)ACETATE;S-2-BENZOTHIAZOLYL-(Z)-2-(TERT-BUTOXYCARBONYL-ISOPROPOXYIMINO)THIOACETATE BENZOTHIAZOLE ESTER;S-2-BENZOTHIAZOLYL (Z)-2-(2-AMINOTHIAZOL-4-YL)-2-(1-T-BUTOXYCARBONYL-1-METHYL)ETHOXYIMINOTHIOACETATE;S-2-BENZOTHIAZOLYL-(2)-2-(1-TERBATOXYCANBONYL-1-METHYLETHOXYIMINO)-4-THIAZOLE ACETATE;(Z)-TERT-BUTYL 2-(1-(2-AMINOTHIAZOL-4-YL)-2-(BENZO[D]THIAZOL-2-YLTHIO)-2-OXOETHYLIDENEAMINOOXY)-2-METHYLPROPANOATE;S-2-benzothiazoyl-(Z)-2-(1-ter-butoxycanbonyl-1-methylethoxyimino)-4-thiazoleacetate;S-2-Benzothiazoyl-(Z)-2-(ter-butoxycarbonyl-isopropoxyimino)-4-thiazoleacetate(TAEM)
• CAS NO: 89604-92-2
• Molecular Formula: C₂₀H₂₂N₄O₄S₃
• Molecular Weight: 478.62
• EINECS: 419-040-9
• Product Categories: Pharmaceutical Intermediates;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 89604-92-2.mol
• Article Data: 4

Chemical Properties

• Melting Point: 138-140°C
• Boiling Point: 621.6 °C at 760 mmHg
• Flash Point: 329.7 °C
• Appearance: /
• Density: 1.41 g/cm³
• Vapor Pressure: 2.26E-15mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Hygroscopic, -20?C Freezer, Under Inert Atmosphere
• Solubility: Chloroform, Methanol
• PKA: 0.83±0.10(Predicted)
• CAS DataBase Reference: 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate(89604-92-2)
• EPA Substance Registry System: 2-Mercaptobenzothiazolyl-(Z)-(2-aminothiazol-4-yl)-2-(tert-butoxycarbonyl) isopropoxyiminoacetate(89604-92-2)

Safety Data

• Statements: 53
• Safety Statements: 61
• Hazardous Substances Data: 89604-92-2(Hazardous Substances Data)

Usage

Chemical Properties

Pale Yellow Solid

Uses

An intermediate for the preparation of cephalosporin derivatives.

InChI:InChI=1/C20H22N4O4S3/c1-19(2,3)27-16(26)20(4,5)28-24-14(12-10-29-17(21)22-12)15(25)31-18-23-11-8-6-7-9-13(11)30-18/h6-10H,1-5H3,(H2,21,22)/b24-14-

Upstream product

• 120-78-5 di(benzothiazol-2-yl)disulfide 
• 86299-47-0 (Z)-2-(2-aminothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxy)iminoacetic acid 

Downstream Products

• 102772-66-7 (Z)-7-(2-(2-aminothiazol-4-yl)-2-(((1-(tertbutoxy)-2-methyl-1-oxopropan-2-yl)oxy)amino)acetamido)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylate 
• 78110-38-0 azthreonam 
• 141555-10-4 7-<2-(aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<2-(3-bromo-4,5-dihydroxyphenyl)ethenyl>ceph-3-em-4-carboxylic acid 
• 141583-27-9 7-<2-(aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-3-<2-(3-bromo-4,5-dihydroxyphenyl)ethenyl>ceph-3-em-4-carboxylic acid 
• 141555-16-0 7-<2-(aminothiazol-4-yl)-2-<(Z)-(1-carboxy-1-methylethoxy)imino>acetamido>-4-<<(4-methoxybenzyl)oxy>carbonyl>-3-<(triphenylphosphonio)methyl>ceph-3-em chloride 
• 141613-43-6 diphenylmethyl 7-<2-(2-aminothiazol-4-yl)-2-<<(Z)-1-(tert-butoxycarbonyl)-1-methylethoxy>imino>acetamido>-3-<<(3-bromo-4,5-diacetoxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylate 
• 141613-44-7 diphenylmethyl 7-<2-(2-aminothiazol-4-yl)-2-<<(Z)-1-(tert-butoxycarbonyl)-1-methylethoxy>imino>acetamido>-3-<<(3,4-diacetoxybenzoyl)oxy>methyl>ceph-3-em-4-carboxylate 

Relevant articles and documents

PRODRUG INHIBITORS

Provided herein are compounds useful as metallo-β-lactamase (MBL) inhibitors. The compounds have a formula A–B, where A is a β-lactam antibiotic moiety comprising a bridging methylene (-CH2-) covalently attached to -B; and B is a latent MBL inhibitor. Also provided are formulations comprising such compounds; as well as such compounds or formulations for use as a medicament. The compounds and formulations may be used in the treatment of antibiotic resistance, bacterial infection. The compounds and formulations may be used in the inhibition of a bacterial MBL.

Green process for synthesizing ceftazidime side-chain active ester by using microwave-assisted method

The invention belongs to the technical field of medicines and in particular relates to a green process for synthesizing a ceftazidime side-chain active ester by using a microwave-assisted method. The green process comprises the following steps: by taking a ceftazidime side-chain acid and dithio-bisbenzothiazole as raw materials, and a mixed solution of benzene and acetonitrile as a solvent, under the catalysis of a composite alkali catalyst, dropwise adding triethyl phosphate, performing a microwave-assisted reaction by using a microwave reactor, and performing aftertreatment after the reaction is completed, thereby obtaining a product, wherein the microwave radiation power is 80-300W, and the radiation time is 30-60 minutes. As triethyl phosphate which is low in price is adopted to replace triphenylphosphine which is high in price in the prior art, the production cost can be reduced. The green process for synthesizing the ceftazidime side-chain active ester by using the microwave-assisted method, which is provided by the invention, is low in cost, the production capacity is greatly increased, the yield is increased, that is, up to 97% or greater, the prepared product is relatively high in purity, that is, up to 99% or greater, and a pleasantly surprised technical effect is achieved.