Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat

Base Information

• Chemical Name: Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat
• CAS No.: 74242-86-7
• Molecular Formula: C₂₈H₂₄Cl₂N₂O₄
• Molecular Weight: 523.416
• Mol file: 74242-86-7.mol

Synonyms:Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat

Chemical Property of Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat

There total 3 articles about Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat 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:

epi-Secopenicillin (67977-61-1,68107-98-2) → Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat (74242-86-7)

Guidance literature:

With chlorine; In ethyl acetate; at 20 - 30 ℃;

DOI:10.1016/S0040-4039(01)85470-8

Reference yield:

6-epipenicillin sulfoxide (69780-18-3) → Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat (74242-86-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PPh₃ / toluene; CH₂Cl₂ / Heating

2: chlorine / ethyl acetate / 20 - 30 °C

With chlorine; triphenylphosphine; In dichloromethane; ethyl acetate; toluene;

DOI:10.1016/S0040-4039(01)85470-8

Reference yield:

→ Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat (74242-86-7)

Guidance literature:

Als Nebenprod. v. Diphenylmethyl-2-(1R,5S-3-phenyl-7-oxo-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-3-methyl-3-butenoat durch Duennschichtchromatographie;

upstream raw materials:

epi-Secopenicillin

6-epipenicillin sulfoxide

Downstream raw materials:

(1R)-6-((3R)-2ξ-chloromethyl-2ξ-methyl-4-oxo-oxetan-3r-yl)-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

(R)-3-chloromethyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester

Diphenylmethyl-2-(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-3,4-dichlor-3-methylbutanoat

(R)-3-Hydroxymethyl-2-((1R,5S)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester