4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide

Base Information

• Chemical Name: 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide
• CAS No.: 54699-97-7
• Molecular Formula: C₂₃H₂₁N₃O₉S
• Molecular Weight: 515.5

Synonyms:4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide

Chemical Property of 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide

Chemical Property:

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Technology Process of 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide

There total 6 articles about 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide 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: 90.22%

4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1S-(β)-oxide (69056-23-1) → 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide (54699-97-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1.5h; Heating;

Reference yield:

(6R)-3t-bromo-3c-methyl-8-oxo-7t-(2-phenoxy-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester (55450-60-7) → 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide (54699-97-7)

Guidance literature:

Multi-step reaction with 3 steps

1: PhICl₂, Py / H₂O / -30 °C

2: MCPBA / CHCl₃

3: Et₃N / CHCl₃

With pyridine; (Dichloroiodo)benzene; triethylamine; 3-chloro-benzenecarboperoxoic acid; In chloroform; water;

DOI:10.1016/S0040-4039(01)94897-X

Reference yield:

(6R)-3t-bromo-3c-methyl-5,5,8-trioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ6-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester (69303-46-4) → 4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1,1-dioxide (54699-97-7)

Guidance literature:

With triethylamine; In chloroform;

DOI:10.1016/S0040-4039(01)94897-X

upstream raw materials:

(6R)-3t-bromo-3c-methyl-5,5,8-trioxo-7t-(2-phenoxy-acetylamino)-(6rH)-5λ⁶-thia-1-aza-bicyclo[4.2.0]octane-2c-carboxylic acid 4-nitro-benzyl ester

4-nitrobenzyl 7β-phenoxyacetamido-3-methyl-3-cephem-4-carboxylate 1S-(β)-oxide

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

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

Downstream raw materials:

(6R,7R)-3-Methyl-4-methylene-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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