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

Base Information

• Chemical Name: (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 144262-08-8
• Molecular Formula: C₂₀H₂₄N₂O₇S
• Molecular Weight: 436.486

Synonyms:(6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property of (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 6 articles about (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-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: 100.0%

t-butyl 3-methyl-7-phenoxyacetamido-2-bromo-3-cephem-4-carboxylate 1,1-dioxide (144262-09-9) → (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (144262-08-8)

Guidance literature:

With potassium acetate; In methanol;

DOI:10.3987/COM-92-6025

Reference yield: 30.0%

(2S,3R,6R,7R)-3,4-Dibromo-3-methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ6-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid tert-butyl ester (144262-07-7) → (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (144262-08-8) + t-butyl 3-methyl-7-phenoxyacetamido-2-bromo-3-cephem-4-carboxylate 1,1-dioxide (144262-09-9)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.3987/COM-92-6025

Reference yield:

tert-butyl-3-methyl-7-phenoxyacetamido-2-cephem-4-carboxylate (24647-38-9) → (6R,7R)-3-Methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (144262-08-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / bromine, Na₂CO₃ / CH₂Cl₂ / 0.08 h / Ambient temperature

2: MCPBA / CH₂Cl₂ / 4 h / Ambient temperature

3: MCPBA / CH₂Cl₂ / 5 h / Heating

4: 52 percent / pyridine / CH₂Cl₂ / Ambient temperature

With pyridine; bromine; sodium carbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.3987/COM-92-6025

upstream raw materials:

t-butyl 3-methyl-7-phenoxyacetamido-2-bromo-3-cephem-4-carboxylate 1,1-dioxide

(2S,3R,6R,7R)-3,4-Dibromo-3-methyl-5,5,8-trioxo-7-(2-phenoxy-acetylamino)-5λ⁶-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid tert-butyl ester

tert-butyl-3-methyl-7-phenoxyacetamido-2-cephem-4-carboxylate

(2S,3R,6R,7R)-3,4-Dibromo-3-methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid tert-butyl ester

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