(6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 257277-40-0
• Molecular Formula: C₄₀H₃₇N₅O₁₀S
• Molecular Weight: 779.827
• Mol file: 257277-40-0.mol

Synonyms:(6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 6 articles about (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-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:

benzhydryl 7-aminocephalosporanate (27266-61-1,54600-89-4) + 2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid (257277-39-7) → (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (257277-40-0)

Guidance literature:

With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jm980648a

Reference yield:

o-nitrobenzyl chloroformate (42854-99-9) → (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (257277-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaOH / dioxane / 0.5 h

2: DCC; HOBt / tetrahydrofuran; CH₂Cl₂ / 24 h / 20 °C

With sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1021/jm980648a

Reference yield:

(4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one (95841-14-8) → (6R,7R)-3-Acetoxymethyl-7-{(R)-2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (257277-40-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: LDA / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 79 percent / hexane; tetrahydrofuran; CH₂Cl₂ / 0.08 h

2.1: 82 percent / aq. LiOH / tetrahydrofuran / 3 h / 0 °C

3.1: 100 percent / CH₂Cl₂ / 0.83 h / 20 °C

4.1: aq. NaOH / dioxane / 0.5 h

5.1: DCC; HOBt / tetrahydrofuran; CH₂Cl₂ / 24 h / 20 °C

With lithium hydroxide; sodium hydroxide; benzotriazol-1-ol; dicyclohexyl-carbodiimide; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane;

DOI:10.1021/jm980648a

upstream raw materials:

benzhydryl 7-aminocephalosporanate

2-[N'-(2-nitro-benzyloxycarbonyl)-hydrazino]-3-phenyl-propionic acid

o-nitrobenzyl chloroformate

(4R,5S)-3-(3-phenylpropionyl)-4-methyl-5-phenyl-oxazolidin-2-one