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

Base Information

• Chemical Name: (6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 27250-44-8
• Molecular Formula: C₁₆H₁₆N₂O₅S
• Molecular Weight: 348.379
• Mol file: 27250-44-8.mol

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

Chemical Property of (6R)-3-methyl-8-oxo-7c-(2-phenoxy-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)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 5 articles about (6R)-3-methyl-8-oxo-7c-(2-phenoxy-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: 93.9%

benzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate (86454-91-3) → (6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (27250-44-8)

Guidance literature:

With sodium bicarbonate; aluminium trichloride; In nitromethane; dichloromethane;

Reference yield:

(6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 2,2,2-trichloro-ethyl ester (27250-43-7) → (6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (27250-44-8)

Guidance literature:

With hydrogenchloride; zinc; In acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(01)98081-5

Reference yield:

1β-oxo-6β-(2-phenoxy-acetylamino)-1λ4-penicillanic acid 2,2,2-trichloro-ethyl ester (30199-55-4) → (6R)-3-methyl-8-oxo-7c-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (27250-44-8)

Guidance literature:

Multi-step reaction with 3 steps

3: Zn, aq. HCl / acetonitrile / Ambient temperature

With hydrogenchloride; zinc; In acetonitrile;

DOI:10.1016/S0040-4039(01)98081-5

upstream raw materials:

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

1β-oxo-6β-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 2,2,2-trichloro-ethyl ester

1β-oxo-6α-(2-phenoxy-acetylamino)-1λ⁴-penicillanic acid 2,2,2-trichloro-ethyl ester

benzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate

Refernces

• 1、 Gutowski. "6-epi-penicillins and 7-epi-cephalosporins.". . p. 1779 - 1782. Retrieved 2007/10/10.