1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 4-(benzoyloxy)-3-chloro-3-(ethylsulfinyl)-6-methyl-7-oxo-, (4-nitrophenyl)methyl ester

Base Information

• Chemical Name: 1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 4-(benzoyloxy)-3-chloro-3-(ethylsulfinyl)-6-methyl-7-oxo-, (4-nitrophenyl)methyl ester
• CAS No.: 137439-99-7
• Molecular Formula: C24H23ClN2O8S
• Molecular Weight: 534.974
• Mol file: 137439-99-7.mol

Synonyms:

Chemical Property of 1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 4-(benzoyloxy)-3-chloro-3-(ethylsulfinyl)-6-methyl-7-oxo-, (4-nitrophenyl)methyl ester

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 4-(benzoyloxy)-3-chloro-3-(ethylsulfinyl)-6-methyl-7-oxo-, (4-nitrophenyl)methyl ester

There total 4 articles about 1-Azabicyclo[3.2.0]heptane-2-carboxylic acid, 4-(benzoyloxy)-3-chloro-3-(ethylsulfinyl)-6-methyl-7-oxo-, (4-nitrophenyl)methyl 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: 65.0%

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-98-6) → p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-chloro-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-99-7)

Guidance literature:

With pyridine; 1,2-Dichloro-3-iodobenzene; In dichloromethane; water; at 0 ℃; for 0.5h;

DOI:10.1039/P19910002399

Reference yield:

p-Nitrobenzyl (4RS,5SR,6SR)-4-benzoyloxy-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (112563-67-4) → p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-chloro-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 66 percent / K₂CO₃ / dimethylformamide / 0.08 h

2: 82 percent / tris(triphenylphosphine)rhodium(I) chloride / CH₂Cl₂ / 16 h / Heating

3: 65 percent / iodobenzene dichloride, pyridine / CH₂Cl₂; H₂O / 0.5 h / 0 °C

With pyridine; Wilkinson's catalyst; 1,2-Dichloro-3-iodobenzene; potassium carbonate; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1039/P19910002399

Reference yield:

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-97-5) → p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-chloro-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate (137439-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / tris(triphenylphosphine)rhodium(I) chloride / CH₂Cl₂ / 16 h / Heating

2: 65 percent / iodobenzene dichloride, pyridine / CH₂Cl₂; H₂O / 0.5 h / 0 °C

With pyridine; Wilkinson's catalyst; 1,2-Dichloro-3-iodobenzene; In dichloromethane; water;

DOI:10.1039/P19910002399

upstream raw materials:

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-6-methyl-7-oxo-1-azabicyclo<3.2.0>heptane-2-carboxylate

p-Nitrobenzyl (4RS,5SR,6SR)-4-benzoyloxy-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

p-Nitrobenzyl (2RS,3SR,4SR,5SR,6SR)-4-benzoyloxy-3-ethylthio-7-oxo-6-(2-oxoethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

Benzoic acid (1S,5R,6S)-7-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-8-oxo-7-aza-bicyclo[4.2.0]oct-3-en-5-yl ester

Downstream raw materials:

p-Nitrobenzyl (4RS,5RS,6RS)-4-benzoyloxy-3-ethylsulphinyl-6-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate