(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

Base Information

• Chemical Name: (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
• CAS No.: 57617-50-2
• Molecular Formula: C₁₇H₁₈N₂O₅S
• Molecular Weight: 362.406
• Mol file: 57617-50-2.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 16.5%

N-phenylacetyl-7α-methoxycephem trichloroethyl ester (61384-40-5) → (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:

With ammonium acetate; zinc; In tetrahydrofuran; at 26 ℃; for 0.416667h;

DOI:10.1021/ja00525a038

Reference yield:

(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) → (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 3 steps

1: 94 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1.) -10 deg C, 1 h, 2.) 26 deg C, 2 h

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

3: 16.5 percent / zinc, 1 M ammonium acetate / tetrahydrofuran; various solvent(s) / 0.42 h / 26 °C

With ammonium acetate; 2-picolinium dichloromethyl phosphonate; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; dichloromethane; toluene;

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:

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

N-phenylacetyl-7α-methoxycephem trichloroethyl ester

(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

(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