(2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 73707-64-9
• Molecular Formula: C₁₇H₁₇Cl₃N₂O₅S₂
• Molecular Weight: 499.823

Synonyms:(2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property of (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

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Technology Process of (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 3 articles about (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl 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: 52.0%

C17H17Cl3N2O4S2 (73707-62-7) → (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73707-64-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 26 ℃; for 2h;

DOI:10.1021/ja00525a038

Reference yield:

6-aminopenicillanic acid trichloroethyl ester p-toluenesulfonate salt (30246-35-6) → (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73707-64-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 80.4 percent / triethylamine, propylene oxide / CH₂Cl₂ / molecular sieves; 1.) 0 deg C, 2 h, 2.) 26 deg C, 0.5 h

2: 58.4 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0-5 deg C, 1 h, 2.) 26 deg C, 12 h

3: 52 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 26 °C

With triethylamine; 3-chloro-benzenecarboperoxoic acid; methyloxirane; In dichloromethane;

DOI:10.1021/ja00525a038

Reference yield:

2S-(2α,5α)-3,3-dimethyl-6-<<(4-methylphenyl)thio>imino>-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid 2,2,2-trichloroethyl ester (67366-05-6) → (2S,5R)-3,3-Dimethyl-4,7-dioxo-6-[(Z)-toluene-4-sulfinylimino]-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73707-64-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 58.4 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 1.) 0-5 deg C, 1 h, 2.) 26 deg C, 12 h

2: 52 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / 26 °C

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/ja00525a038

upstream raw materials:

C₁₇H₁₇Cl₃N₂O₄S₂

6-aminopenicillanic acid trichloroethyl ester p-toluenesulfonate salt

2S-(2α,5α)-3,3-dimethyl-6-<<(4-methylphenyl)thio>imino>-7-oxo-4-thia-1-azabicyclo<3.2.0>heptane-2-carboxylic acid 2,2,2-trichloroethyl ester

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