(2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 73745-53-6
• Molecular Formula: C₁₉H₂₁Cl₃N₂O₆S
• Molecular Weight: 511.811

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

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

Chemical Property:

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

There total 1 articles about (2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-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: 94.0%

(2S,5R,6S)-6-Methoxy-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (64308-55-0) → (2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73745-53-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; 1.) -10 deg C, 1 h, 2.) 26 deg C, 2 h;

DOI:10.1021/ja00525a038

Reference yield: 24.0%

(2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73745-53-6) → N-phenylacetyl-7α-methoxycephem trichloroethyl ester (61384-40-5)

Guidance literature:

With 2-picolinium dichloromethyl phosphonate; In toluene; for 10h; Heating;

DOI:10.1021/ja00525a038

Reference yield:

(2S,4S,5R,6S)-6-Methoxy-3,3-dimethyl-4,7-dioxo-6-phenylacetylamino-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester (73745-53-6) → (6R)-7c-methoxy-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (57617-50-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / 2-picolinium dichloromethyl phosphonate / toluene / 10 h / Heating

2: 16.5 percent / zinc, 1 M ammonium acetate / tetrahydrofuran; various solvent(s) / 0.42 h / 26 °C

With ammonium acetate; 2-picolinium dichloromethyl phosphonate; zinc; In tetrahydrofuran; toluene;

DOI:10.1021/ja00525a038

upstream raw materials:

(2S,5R,6S)-6-Methoxy-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Downstream raw materials:

N-phenylacetyl-7α-methoxycephem trichloroethyl ester

(6R)-7c-methoxy-3-methyl-8-oxo-7t-(2-phenyl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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