(6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 61375-82-4
• Molecular Formula: C₂₃H₂₁N₃O₈S
• Molecular Weight: 499.501

Synonyms:(6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester

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Technology Process of (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester

There total 4 articles about (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl 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:

→ p-Nitrobenzyl 7-(phenoxyacetamido)-3-methylenecepham-4-carboxylate 1β-oxide (60771-27-9,61375-82-4,63427-57-6,69308-55-0,87303-96-6,119944-11-5)

Guidance literature:

aus entspr. Sulfoxid II mit PBr3;

DOI:10.1021/ja00432a068

Reference yield:

→ (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester (60771-27-9,61375-82-4,63427-57-6,69308-55-0,87303-96-6,119944-11-5)

Guidance literature:

aus 6-Phenoxyacetylaminopenicillansaeure-(4-nitrobenzyl)ester-1-oxid, N-Chlorsuccinimid, SnCl4;

Reference yield:

(R)-2-[(2R,3R)-2-Chlorosulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester (61375-83-5) → (6R)-3-methylene-5ξ,8-dioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester (61375-82-4)

Guidance literature:

With methanol; zinc chloride diethyl ether; isopropyl alcohol; Yield given. Multistep reaction; 1.) CH₂Cl₂, toluene, di-n-butyl ether, a) 0-5 deg C, 30 min, b) 20-25 deg C, 5 h;

DOI:10.1080/00397919508013425

upstream raw materials:

(R)-2-[(2R,3R)-2-Chlorosulfinyl-4-oxo-3-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid 4-nitro-benzyl ester

Downstream raw materials:

(6R)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R)-3-acetoxymethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R)-3-iodomethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(6R)-3-bromomethyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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