36923-21-4

Basic information

• Product Name: 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester
• Synonyms: 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester;7-AICA;7-Amino-3-Chloro-3-Cephem-4-Carboxylicacid-4-benzhydrylester;DiphenylMethyl 7β-AMino-3-cepheM-4-carboxylate;7-AMINO-8-OXO-5-THIA-1-AZABICYCLO[4.2.0]OCT-2-ENE-;(6R,7R)-7-AMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid DiphenylMethyl Ester;(6R-trans)-7-AMino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid DiphenylMethyl Ester;(6R,7R)-Benzhydryl 7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS NO: 36923-21-4
• Molecular Formula: C₂₀H₁₈N₂O₃S
• Molecular Weight: 366.43
• EINECS: 1312995-182-4
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 36923-21-4.mol
• Article Data: 6

Chemical Properties

• Melting Point: 164.0 to 168.0 °C
• Boiling Point: 587.751 °C at 760 mmHg
• Flash Point: 309.261 °C
• Appearance: /
• Density: 1.39
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.701
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly, Heated)
• PKA: 4.97±0.40(Predicted)
• CAS DataBase Reference: 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester(36923-21-4)
• EPA Substance Registry System: 7-Amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester(36923-21-4)

Safety Data

• Hazardous Substances Data: 36923-21-4(Hazardous Substances Data)

Usage

Uses

An intermediate in the preparation of cephems: beta-lactam antibiotics.

InChI:InChI=1/C20H18N2O3S/c21-16-18(23)22-15(11-12-26-19(16)22)20(24)25-17(13-7-3-1-4-8-13)14-9-5-2-6-10-14/h1-11,16-17,19H,12,21H2

Upstream product

• 51762-51-7 (6R)-3ξ-hydroxy-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid benzhydryl ester 
• 35246-65-2 (6R)-3-formyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester 
• 35246-64-1 (6R,7R)-benzhydryl 3-(hydroxymethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate 
• 36923-17-8 (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 908093-98-1 diazodiphenylmethane 

Downstream Products

• 158743-75-0 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-methyl-2-pentenoylamino>-3-cephem-4-carboxylate 
• 158743-74-9 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-hexenoylamino>-3-cephem-4-carboxylate 
• 158743-76-1 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-3-cyclopropyl-2-propenoylamino>-3-cephem-4-carboxylate 
• 158743-78-3 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-3-cyclopentyl-2-propenoylamino>-3-cephem-4-carboxylate 
• 158743-82-9 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-5-phenyl-2-pentenoylamino>-3-cephem-4-carboxylate 
• 158743-87-4 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,3,4-thiadiazol-2-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate 
• 158743-85-2 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-(1,2,3-thiadiazol-5-ylthio)-2-butenoylamino>-3-cephem-4-carboxylate 
• 158743-88-5 diphenylmethyl 7β-<(E)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-butenoylamino>-3-cephem-4-carboxylate 
• 86978-44-1 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-2-butenoylamino>-3-cephem-4-carboxylate 
• 158743-79-4 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-cyclopentyl-2-butenoylamino>-3-cephem-4-carboxylate 
• 158743-81-8 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-3-phenyl-2-propenoylamino>-3-cephem-4-carboxylate 
• 158743-80-7 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-cyclohexyl-2-butenoylamino>-3-cephem-4-carboxylate 
• 158743-83-0 diphenylmethyl 7β-<(Z)-2-(2-tert-butoxycarbonylaminothiazol-4-yl)-4-phenyl-2-butenoylamino>-3-cephem-4-carboxylate 
• 171017-68-8 (6R,7R)-7-<2-(3-hydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester 

Relevant articles and documents

Ceftibuten: Development of a commercial process based on cephalosporin C. Part III. Process for the conversion of 3-exomethylene-7(R)-glutaroylaminocepham-4-carboxylic acid 1(S)-oxide to Ceftibuten

The foregoing papers (Bernasconi, E.; Lee, J.; Roletto, J.; Sogli, L.; Walker, D. Org. Process Res. Dev. 2002, 6, 152 and Bernasconi, E.; Genders, D.; Lee, J.; Longoni, D.; Martin, C. R.; Menon, V.; Roletto, J.; Sogli, L.; Walker, D.; Zappi, G.; Zelenay, P.; Zhang, H. Org. Process Res. Dev. 2002, 6, 158) describe a high-yielding, all-aqueous process for the preparation of 3-exomethylene-7(R)-glutaroylaminocepham-4-carboxylic acid 1(S)-oxide (3) from fermented cephalosporin C broth via enzyme transformations and electrochemical reduction without isolation of any precursors. In this paper we describe the efficient recovery of 3 from aqueous solution, by extractive esterification employing diphenyldiazomethane, and the conversion of the obtained bis(diphenylmethyl) ester (4) into intermediates both for Ceftibuten (1) and cefaclor (8). Several routes to the key Ceftibuten building block, diphenylmethyl 7(R)-aminoceph-3-em-4-carboxylate (6) are described. This key building block is acylated, deblocked, and purified using chemistry described by Shionogi workers to give Ceftibuten.

Production of 3-allyl- and 3-butenyl-3-cephems

There is disclosed a process for the production of certain 2-allyl- and 3-butenyl-3-cephem derivatives by coupling a 3-chloromethyl-3-cephem with a hydrocarbyltributystannane in the presence of bis(dibenzylideneacetonyl)-palladium and a phosphine. The 3-allyl- and 3-butenyl-3-cephem derivatives so-produced are useful as broad-spectrum antibacterial agents.