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

Base Information

• Chemical Name: (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester
• CAS No.: 123054-30-8
• Molecular Formula: C₂₄H₂₁F₃N₂O₈S₂
• Molecular Weight: 586.567
• Mol file: 123054-30-8.mol

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

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

Chemical Property:

Purity/Quality:

98% HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-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:

trifluoromethylsulfonic anhydride (358-23-6) + p-methoxybenzyl 7β-phenylacetylamino-3-hydroxy-3-cephem-4-carboxylate (123054-31-9) → (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.7164/antibiotics.54.257

Reference yield:

(E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-hydroxy-but-2-enoic acid 4-methoxy-benzyl ester (131857-34-6) → (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N / CH₂Cl₂ / 1 h / -78 °C

2: 7 percent Chromat_. / PbBr₂, Al / dimethylformamide / 2.1 h / Ambient temperature

With lead(II) bromide; triethylamine; aluminium; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo970051n

Reference yield:

p-methoxybenzyl (E)-3-chloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-4-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate (168418-30-2) → (7R)-7-[(phenylacetyl)amino]-3-trifluoromethanesulfonyloxy-3-cephem-4-carboxylate, 4-methoxybenzyl ester (123054-30-8) + 3-methylene-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-methoxybenzyl ester (139371-98-5)

Guidance literature:

With lead(II) bromide; aluminium; In N,N-dimethyl-formamide; for 2.1h; Ambient temperature;

DOI:10.1021/jo970051n

upstream raw materials:

p-methoxybenzyl (E)-3-chloro-2-<2-oxo-3-(phenylacetamido)-4-<(phenylsulfonyl)thio>azetidin-1-yl>-4-<<(trifluoromethyl)sulfonyl>oxy>-2-butenoate

trifluoromethylsulfonic anhydride

p-methoxybenzyl 7β-phenylacetylamino-3-hydroxy-3-cephem-4-carboxylate

(E)-2-((2R,3R)-2-Benzenesulfonylsulfanyl-4-oxo-3-phenylacetylamino-azetidin-1-yl)-4-chloro-3-hydroxy-but-2-enoic acid 4-methoxy-benzyl ester

Downstream raw materials:

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

(6R,7R)-3-(2-Methyl-propenyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(7R,8R)-7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester

(6R,7R)-3-(4-Methoxy-phenyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester