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

Base Information

• Chemical Name: (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester
• CAS No.: 54639-47-3
• Molecular Formula: C₂₉H₂₆N₂O₅S
• Molecular Weight: 514.602

Synonyms:(6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

Chemical Property of (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Technology Process of (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester

There total 1 articles about (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl 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:

7-Phenoxyacetamido-3-exo-methylene cepham (40849-60-3) + diazodiphenylmethane (908093-98-1) → (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester (54639-47-3)

Guidance literature:

In benzene;

DOI:10.1002/hlca.19740570705

Reference yield: 28.0%

N-aminophthalamide (1875-48-5) + (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester (54639-47-3) → (2R,7R,8R)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methylene-9-oxo-8-(2-phenoxy-acetylamino)-6-thia-1,5-diaza-bicyclo[5.2.0]nonane-2-carboxylic acid benzhydryl ester (139396-62-6) + (R)-2-[(2R,3R)-2-[N-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)aminosulfanyl]-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-{[(E)-1,3-dioxo-1,3-dihydro-isoindol-2-ylimino]-methyl}-but-3-enoic acid benzhydryl ester

Guidance literature:

With lead(IV) acetate; In dichloromethane; for 0.5h; Mechanism; var. 3-exomethylenecepham sulfides;

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + (6R)-3-methylene-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid benzhydryl ester (54639-47-3) → benzhydryl 3-methoxy-7β-(2-phenoxyacetamido)-Δ3-cephem-4-carboxylate (54639-52-0)

Guidance literature:

Multistep reaction; (i) O₂, O₃, CH₂Cl₂, (ii) Me₂S, (iii) /BRN= 102415/, Et₂O;

DOI:10.1002/hlca.19740570705

upstream raw materials:

7-Phenoxyacetamido-3-exo-methylene cepham

diazodiphenylmethane

Downstream raw materials:

benzhydryl 3-methoxy-7β-(2-phenoxyacetamido)-Δ³-cephem-4-carboxylate

(2R,7R,8R)-5-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methylene-9-oxo-8-(2-phenoxy-acetylamino)-6-thia-1,5-diaza-bicyclo[5.2.0]nonane-2-carboxylic acid benzhydryl ester

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

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