90467-27-9

Basic information

• Product Name: 7β-[(2-Hydroxybenzylidene)amino]-3-(hydroxymethyl)cepham-3-ene-4-carboxylic acid diphenylmethyl ester
• Synonyms: (6R,7R)-3-Hydroxymethyl-8-oxo-7α-salicylideneamino-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester;7β-[(2-Hydroxybenzylidene)amino]-3-(hydroxymethyl)cepham-3-ene-4-carboxylic acid diphenylmethyl ester
• CAS NO: 90467-27-9
• Molecular Formula: C₂₈H₂₄N₂O₅S
• Molecular Weight: 500.56556
• Mol File: 90467-27-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 754.5°C at 760 mmHg
• Flash Point: 410.1°C
• Appearance: /
• Density: 1.36g/cm³
• Vapor Pressure: 6.39E-24mmHg at 25°C
• Refractive Index: 1.681
• CAS DataBase Reference: 7β-[(2-Hydroxybenzylidene)amino]-3-(hydroxymethyl)cepham-3-ene-4-carboxylic acid diphenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7β-[(2-Hydroxybenzylidene)amino]-3-(hydroxymethyl)cepham-3-ene-4-carboxylic acid diphenylmethyl ester(90467-27-9)
• EPA Substance Registry System: 7β-[(2-Hydroxybenzylidene)amino]-3-(hydroxymethyl)cepham-3-ene-4-carboxylic acid diphenylmethyl ester(90467-27-9)

Safety Data

• Hazardous Substances Data: 90467-27-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C28H24N2O5S/c31-16-21-17-36-27-23(29-15-20-13-7-8-14-22(20)32)26(33)30(27)24(21)28(34)35-25(18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-15,23,25,27,31-32H,16-17H2/b29-15+/t23-,27-/m1/s1

Upstream product

• 15690-38-7 (6R,7R)-7-amino-3-hydroxymethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 89-95-2 2-methyl-benzyl alcohol 
• 908093-98-1 diazodiphenylmethane 
• 90467-24-6 (6R,7R)-3-Hydroxymethyl-7-{[1-(2-hydroxy-phenyl)-meth-(E)-ylidene]-amino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 

Downstream Products

• 128989-86-6 diphenylmethyl 7β-(o-hydroxybenzylideneamino)-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 128989-84-4 diphenylmethyl 7α-amino-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 128999-45-1 diphenylmethyl 7β-amino-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 128989-85-5 potassium 7α-phenylacetamido-3-cyano-3-cephem-4-carboxylate 
• 128989-92-4 diphenylmethyl 7α-phenylacetamido-3-t-butyldimethylsilyloxymethyl-3-cephem-4-carboxylate 
• 128989-94-6 diphenylmethyl 7α-phenylacetamido-3-hydroxyiminomethyl-3-cephem-4-carboxylate 
• 128989-88-8 diphenylmethyl 7β-isocyano-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 128989-93-5 diphenylmethyl 7α-phenylacetamido-3-formyl-3-cephem-4-carboxylate 
• 128989-95-7 diphenylmethyl 7α-phenylacetamido-3-cyano-3-cephem-4-carboxylate 
• 128989-87-7 diphenylmethyl 7β-formamido-3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 128989-89-9 diphenylmethyl 3-t-butyldimethylsiloxymethyl-3-cephem-4-carboxylate 
• 129006-07-1 diphenylmethyl 3-hydroxyiminomethyl-3-cephem-4-carboxylate 
• 128989-91-3 diphenylmethyl 3-cyano-3-cephem-4-carboxylate 
• 128989-90-2 diphenylmethyl 3-formyl-3-cephem-4-carboxylate 

Relevant articles and documents

Improvement of the synthesis of diphenylmethyl 7β-(o-hydroxy)benzylideneamino-3-hydroxymethyl-3-cephem-4-carboxylate

The title product (I) is synthesized currently from 7-aminocephalosporanic acid, and diphenyldiazomethane (DDM) is used as a protective reagent of the acid function for further reactions. When DDM was prepared from benzophenone hydrazone by reaction with chloramine T, it was resulted impure by p-toluenesulfonamide, formed as side product, which cannot be removed during the final purification step carried out according to the literature procedure. Two simple methods are proposed here to obtain I with the suitable degree of purity necessary for a drug.