5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, diphenylmethyl ester, (6R,7R)-

Base Information

• Chemical Name: 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, diphenylmethyl ester, (6R,7R)-
• CAS No.: 27266-61-1
• Molecular Formula: C₂₃H₂₂N₂O₅S
• Molecular Weight: 438.504
• Mol file: 27266-61-1.mol

Synonyms:benzhydryl 7-aminocephalosporinate;7β-amino-cephalosporanic acid benzhydryl ester;benzhydryl 7-aminocephalosporanate;diphenylmethyl 7-aminocephalosporanate;7-aminocephalosporanic acid diphenylmethyl ester;(6R)-3-acetoxymethyl-7t-amino-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester;

Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, diphenylmethyl ester, (6R,7R)-

Chemical Property:

• Melting Point: 122-124 °C
• Boiling Point: 638.7±55.0 °C(Predicted)
• PSA: 124.23000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 3.01700

Purity/Quality:

7-AminocephalosporanicAcidDiphenylmethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (7-Aminocephalosporanic acid diphenylmethyl ester is an intermediate in the synthesis of Cefmetazole (C242850), which is a semi-synthetic antibiotic derived from Cephamycin. Antibacterial.

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, diphenylmethyl ester, (6R,7R)-

There total 9 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-amino-8-oxo-, diphenylmethyl ester, (6R,7R)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 82.0%

7-Aminocephalosporanic acid (957-68-6) + diazodiphenylmethane (908093-98-1) → benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4)

Guidance literature:

With toluene-4-sulfonic acid; In water; acetonitrile; at 20 ℃; for 1h; pH=3; Inert atmosphere;

DOI:10.1002/anie.201107810

Reference yield: 65.0%

methanol (67-56-1) + 7-Aminocephalosporanic acid (957-68-6) + diazodiphenylmethane (908093-98-1) → benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4) + benzhydryl methyl ether (1016-09-7)

Guidance literature:

In dichloromethane; at 20 ℃; for 72h;

DOI:10.1021/jo048970i

Reference yield: 65.0%

diazodiphenylmethane (908093-98-1) + 7β-Aminocephalosporanic acid (1214622-93-1) → Benzhydryl 7β-aminocephalosporanate (27266-61-1,54600-89-4)

Guidance literature:

In methanol; dichloromethane; Ambient temperature;

upstream raw materials:

triphenyl phosphite

(6R)-3-acetoxymethyl-7t-((R)-5-amino-5-benzhydryloxycarbonyl-pentanoylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

7-Aminocephalosporanic acid

diazodiphenylmethane

Downstream raw materials:

benzhydryl 7-oxocephalosporanate

benzhydryl 7-diazocephalosporanate

Benzhydryl 7β-(α-methoxybenzylideneamino)-cephalosporanate

(6R,7R)-3-acetyloxymethyl-7-<2-(2,6-dihydroxyphenyl)-4-thiazolyl>acetylamino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid diphenylmethyl ester