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

Base Information

• Chemical Name: (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 54055-49-1
• Molecular Formula: C₁₈H₁₇N₃O₉S
• Molecular Weight: 451.414

Synonyms:(6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

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Technology Process of (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 3 articles about (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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: 74.4%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + 3-acetoxymethyl-7-aminoceph-3-em-4-carboxylic acid + 4-nitrobenzyl chloroformate (4457-32-3) → (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (54055-49-1)

Guidance literature:

With pyridine; In dichloromethane; water; ethyl acetate;

Reference yield:

7β-Aminocephalosporanic acid (1214622-93-1) + 4-nitrobenzyl chloroformate (4457-32-3) → (6R)-3-acetoxymethyl-7t-(4-nitro-benzyloxycarbonylamino)-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (54055-49-1)

Guidance literature:

Multistep reaction; (i) bis(trimethylsilyl)acetamide, MeCN, (ii) /BRN= 912446/;

DOI:10.1016/S0040-4039(01)82475-8

Reference yield:

→ 3-Acetoxymethyl-7-(4-nitro-benzyloxycarbonylamino)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (54055-49-1)

Guidance literature:

entspr. Cephalosporansaeure,Bis-trimethylsilyl-acetamid,Chlorameisensaeure-p-nitrobenzylester;

upstream raw materials:

7β-Aminocephalosporanic acid

4-nitrobenzyl chloroformate

N,O-bis-(trimethylsilyl)-acetamide

Downstream raw materials:

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

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

(6R)-3-acetoxymethyl-7t-(4-amino-benzyloxycarbonylamino)-7c-methoxy-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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

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