(6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Base Information

• Chemical Name: (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester
• CAS No.: 27250-45-9
• Molecular Formula: C₁₈H₁₇Cl₃N₂O₆S
• Molecular Weight: 495.768

Synonyms:(6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property of (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

Chemical Property:

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Technology Process of (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

There total 2 articles about (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-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: 83.0%

2,2,2-Trichloroethyl (6R,7R)-3-methyl-<(phenoxyacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate (24647-47-0) → (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester (27250-45-9)

Guidance literature:

With dihydrogen peroxide; acetic acid; In dichloromethane; for 24h; Ambient temperature;

Reference yield:

→ (6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester (27250-45-9)

Guidance literature:

Trichlorethylester (Bsp.1),m-Chlorperbenzoesaeure;

Reference yield:

(6R)-3-methyl-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester (27250-45-9) → (6R)-3,4t-dimethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (31932-93-1)

Guidance literature:

Multi-step reaction with 4 steps

1: Me₂NH*HCl / CH₂Cl₂; 2-methyl-propan-2-ol; H₂O

2: H₂ / Rh-C / ethyl acetate; acetic acid

3: SnCl₂, AcCl / CH₂Cl₂; acetonitrile

4: aq. HCO₂H, Zn

With formic acid; hydrogen; N,N-dimethylammonium chloride; acetyl chloride; tin(ll) chloride; zinc; Rh on carbon; In dichloromethane; water; acetic acid; ethyl acetate; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm00287a011

upstream raw materials:

2,2,2-Trichloroethyl (6R,7R)-3-methyl-<(phenoxyacetyl)amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate

Downstream raw materials:

2,2,2-trichloroethyl 7β-phenoxyacetamido-2-methylene-3-methyl-3-cephem-4-carboxylate 1S-(β)-oxide

(6R)-3-methyl-4-methylene-5t,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester

(6R)-3,4-dimethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2ξ-carboxylic acid

(6R)-3ξ-methyl-4-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2ξ-carboxylic acid

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