7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid

Base Information

• Chemical Name: 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid
• CAS No.: 123077-99-6
• Molecular Formula: C₁₇H₁₅F₃N₂O₈S
• Molecular Weight: 464.376
• Mol file: 123077-99-6.mol

Synonyms:7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid

Chemical Property of 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid

There total 2 articles about 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid 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:

p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate (108493-71-6) → 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid (123077-99-6)

Guidance literature:

With hydrogenchloride; zinc; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1021/jm00168a019

Reference yield:

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate (119892-46-5) → 7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid (123077-99-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.5 g / Et₃N / CH₂Cl₂ / 0.08 h / -40 °C

2: 15.07 g / Zn, 1 N HCl / dimethylformamide; tetrahydrofuran / 4 h / Ambient temperature

With hydrogenchloride; triethylamine; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00131a005

Reference yield: 75.0%

7β-[(phenoxyacetyl)amino]-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylic acid (123077-99-6) + diazodiphenylmethane (908093-98-1) → diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate (123078-32-0)

Guidance literature:

In acetonitrile; for 2h; Ambient temperature;

DOI:10.1021/jm00131a005

upstream raw materials:

p-nitrobenzyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

p-nitrobenzyl 7β-[(phenoxyacetyl)amino]-3-hydroxy-1-carba-1-dethia-3-cephem-4-carboxylate

Downstream raw materials:

allyl 7β-(phenoxyacetamido)-3-<<(trifluoromethyl)sulfonyl>oxy>-1-carba-1-dethia-3-cephem-4-carboxylate

diphenylmethyl (7S,6R)-7-(phenoxyacetamido)-3-{[(trifluoromethyl)sulfonyl]oxy}-1-carba-1-dethia-3-cephem-4-carboxylate

(6R,7S)-3-Bromo-8-oxo-7-(2-phenoxy-acetylamino)-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

(6R,7S)-7-tert-Butoxycarbonylamino-8-oxo-3-trifluoromethyl-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester