7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

Base Information

• Chemical Name: 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester
• CAS No.: 119608-90-1
• Molecular Formula: C₂₅H₂₄N₂O₅S
• Molecular Weight: 464.542
• Mol file: 119608-90-1.mol

Synonyms:7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

Chemical Property of 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

Chemical Property:

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester

There total 6 articles about 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester 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: 84.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester (104146-10-3) → 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester (119608-90-1)

Guidance literature:

(6R,7R)-3-Chloromethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester; With hydrogenchloride; triphenylphosphine; sodium iodide; In dichloromethane; water; at 32 - 36 ℃; pH=3; Large scale reaction;

formaldehyd; With sodium hydroxide; In dichloromethane; water; N,N-dimethyl-formamide; at 10 - 20 ℃; Large scale reaction;

DOI:10.1021/op900053j

Reference yield: 70.0%

tri-n-butyl(vinyl)tin (7486-35-3) + 2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester (139472-60-9) → 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester (119608-90-1)

Guidance literature:

With 1-methyl-pyrrolidin-2-one; copper(l) chloride; for 1h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60924-3

Reference yield: 61.0%

tri-n-butyl(vinyl)tin (7486-35-3) + p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate (168418-31-3) → 7-(phenylacetyl)amino-3-vinyl-4-cephalosporanic acid p-methoxybenzyl ester (119608-90-1) + (6R,7R)-3-Benzenesulfonyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Guidance literature:

With 1,10-Phenanthroline; copper(l) chloride; In various solvent(s); for 2h; Yields of byproduct given; Ambient temperature;

DOI:10.1055/s-1999-2735

upstream raw materials:

tri-n-butyl(vinyl)tin

(7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester

2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-buta-2,3-dienoic acid 4-methoxy-benzyl ester

p-methoxybenzyl (E)-3,4-dichloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-2-butenoate

Downstream raw materials:

7-(phenylacetamido)-3-vinylcephem-4-carboxylic acid

(6R,7R)-7-amino-3-vinyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid