(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester
• CAS No.: 76227-88-8
• Molecular Formula: C₁₅H₁₄N₂O₅S
• Molecular Weight: 334.353

Synonyms:(5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Chemical Property of (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester

There total 19 articles about (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl 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: 46.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 2-oxo-bisnorpenicillin G-3-carboxylic acid (78815-39-1) → 2-oxo-bisnorpenicillin G-3-methyl carboxylate (76227-88-8)

Guidance literature:

In tetrahydrofuran; diethyl ether; for 1h; -20 deg C -> r. t.;

DOI:10.1016/S0040-4020(01)92143-X

Reference yield: 36.0%

2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monomethyl ester (76227-85-5,78855-23-9,78855-24-0) → (5R,6R)-3,7-Dioxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid methyl ester (76227-88-8)

Guidance literature:

With diisopropyl-carbodiimide; In dichloromethane; at -60 - 20 ℃;

DOI:10.1016/S0040-4039(00)77414-4

Reference yield: 36.0%

2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monomethyl ester (76227-85-5,78855-23-9,78855-24-0) → 2-oxo-bisnorpenicillin G-3-methyl carboxylate (76227-88-8)

Guidance literature:

With diisopropyl-carbodiimide; In dichloromethane; -60 deg C -> 20 deg C, 5 h;

DOI:10.1016/S0040-4020(01)92143-X

upstream raw materials:

2-((2R,3R)-2-Mercapto-4-oxo-3-phenylacetylamino-azetidin-1-yl)-malonic acid monomethyl ester

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-methyl malonate

diazomethane

2-oxo-bisnorpenicillin G-3-carboxylic acid

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