(2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 51416-07-0
• Molecular Formula: C₂₉H₂₇ClN₂O₆S
• Molecular Weight: 567.062

Synonyms:

Chemical Property of (2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 2 articles about (2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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:

10-chloro-6β-(2-phenoxy-acetylamino)-penicillanic acid benzhydryl ester (51415-41-9) → 10-chloro-1α-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid benzhydryl ester (51416-07-0)

Guidance literature:

Multistep reaction; (i) aq. NaOAc, N₂O₄, CH₂Cl₂, (ii) MCPBA, (iii) Zn, AcOH;

Reference yield:

→ 10-chloro-1α-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid benzhydryl ester (51416-07-0)

Guidance literature:

corresp. N-nitroso-cpd., Zn;

Reference yield: 73.0%

(2S,3R,4R,6R)-3-Chloromethyl-3-methyl-4,7-dioxo-6-(2-phenoxy-acetylamino)-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (51416-06-9,51416-07-0,51416-20-7,80339-53-3) → (R)-3-Chloromethyl-2-((1S,5R)-7-oxo-3-phenoxymethyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester (78037-20-4)

Guidance literature:

With triphenylphosphine; squaric acid; In benzene; for 0.25h; Heating;

DOI:10.1016/S0040-4039(01)81835-9

upstream raw materials:

10-chloro-6β-(2-phenoxy-acetylamino)-penicillanic acid benzhydryl ester

Downstream raw materials:

10-bromo-9-chloro-6β-(2-phenoxy-acetylamino)-penicillanic acid benzhydryl ester

(6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

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

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