(6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 244009-24-3
• Molecular Formula: C₂₄H₃₁N₃O₇S
• Molecular Weight: 505.592
• Mol file: 244009-24-3.mol

Synonyms:(6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property of (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 4 articles about (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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: 42.0%

7-Aminocephalosporanic acid t-butyl ester (6187-87-7) + α-N-benzyloxyamino-propionic acid (54837-15-9) → (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (244009-24-3)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0014-827X(99)00017-8

Reference yield:

N-Benzyloxy-DL-alanin-ethylester (21653-11-2) → (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (244009-24-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 61 percent / NaOH; H₂O / tetrahydrofuran / 0 °C

2: 42 percent / EDCI / CH₂Cl₂ / 12 h / 20 °C

With sodium hydroxide; water; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Acylation;

DOI:10.1016/S0014-827X(99)00017-8

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → (6R,7R)-3-Acetoxymethyl-7-(2-benzyloxyamino-propionylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (244009-24-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / AcONa / ethanol / 24 h / 20 °C

2: 69 percent / BH₃*NEt₃; HCl / ethanol / 20 h / 0 °C

3: 61 percent / NaOH; H₂O / tetrahydrofuran / 0 °C

4: 42 percent / EDCI / CH₂Cl₂ / 12 h / 20 °C

With hydrogenchloride; sodium hydroxide; triethylamine-borane; water; sodium acetate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; ethanol; dichloromethane; 1: Condensation / 2: Reduction / 3: Hydrolysis / 4: Acylation;

DOI:10.1016/S0014-827X(99)00017-8

upstream raw materials:

7-Aminocephalosporanic acid t-butyl ester

α-N-benzyloxyamino-propionic acid

N-Benzyloxy-DL-alanin-ethylester

O-benzylhydoxylamine hydrochloride