(2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

Base Information

• Chemical Name: (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester
• CAS No.: 80127-25-9
• Molecular Formula: C₁₉H₂₁ClN₂O₅S
• Molecular Weight: 424.905

Synonyms:(2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

Chemical Property of (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

Chemical Property:

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Technology Process of (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester

There total 3 articles about (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl 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:

2-chloro-2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate (76627-82-2) → (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester (80127-25-9)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1021/jo00342a048

Reference yield:

Penicillin G potassium (113-98-4) → (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester (80127-25-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / sodium iodide / dimethylformamide / 20 h / 25 °C

2: m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂

With 3-chloro-benzenecarboperoxoic acid; sodium iodide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00342a048

Reference yield:

allyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (80127-23-7) → (2S,5R,6R)-3,3-Dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2-chloro-allyl ester (80127-25-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / potassium 2-ethylhexanoate, tetrakis(triphenylphosphine)palladium, PPh₃ / ethyl acetate / 2 h / 25 °C

2: 94 percent / sodium iodide / dimethylformamide / 20 h / 25 °C

3: m-chloroperbenzoic acid (MCPBA) / CH₂Cl₂

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium 2-ethylhexanoate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00342a048

upstream raw materials:

2-chloro-2-propenyl (3S,5R,6R)-2,2-dimethyl-6-(phenylacetamido)-7-oxopenam-3-carboxylate

Penicillin G potassium

allyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenylacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Downstream raw materials:

2-chloro-2-propenyl (6R,7R)-3-methyl-7-(phenylacetamido)-8-oxo-3-cephem-4-carboxylate

7-phenylacetamidodesacetoxycephalosporanic acid

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