(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Base Information

Chemical Name:(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester
CAS No.:111924-31-3
Molecular Formula:C₂₃H₂₀ClN₃O₈S
Molecular Weight:533.946
Hs Code.:

(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

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Chemical Property of (2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

There total 3 articles about (2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl 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:

: 70850-45-2
10-hydroxy-1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 4-nitro-benzyl ester

: 111924-31-3
(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 85 percent / dimethyl sulphoxide / acetic anhydride / 20 °C

2: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

3: 66 percent / PBr₃ / dimethylformamide / 0 °C

4: oxalyl chloride, 2,6-lutidine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With 2,6-dimethylpyridine; sodium chlorite; oxalyl dichloride; phosphorus tribromide; dimethyl sulfoxide; recorcinol; In tetrahydrofuran; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide;
DOI:10.1039/c39870000081

Reference yield:

: 111924-23-3
(2S,3R,4S,5R,6R)-3-Formyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

: 111924-31-3
(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / sodium chlorite, resorcinol / tetrahydrofuran; H₂O; various solvent(s) / pH 3.5

2: 66 percent / PBr₃ / dimethylformamide / 0 °C

3: oxalyl chloride, 2,6-lutidine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With 2,6-dimethylpyridine; sodium chlorite; oxalyl dichloride; phosphorus tribromide; recorcinol; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1039/c39870000081

Reference yield:

: 111924-24-4
(2S,3R,4S,5R,6R)-3-Methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-(4-nitro-benzyl) ester

: 111924-31-3
(2S,3R,5R,6R)-3-Chlorocarbonyl-3-methyl-7-oxo-6-(2-phenoxy-acetylamino)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / PBr₃ / dimethylformamide / 0 °C

2: oxalyl chloride, 2,6-lutidine / CH₂Cl₂ / 1.) 0 deg C, 2.) 16 h, room temperature

With 2,6-dimethylpyridine; oxalyl dichloride; phosphorus tribromide; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c39870000081