4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide

Base Information

• Chemical Name: 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide
• CAS No.: 95570-58-4
• Molecular Formula: C₁₉H₁₉NO₁₀S
• Molecular Weight: 453.427
• Mol file: 95570-58-4.mol

Synonyms:4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide

Chemical Property of 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide

There total 6 articles about 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-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: 84.0%

4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide (128472-66-2) → 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide (95570-58-4)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; at 0 ℃; for 0.5h;

DOI:10.1021/jm00171a029

Reference yield:

4-hydroxymethylbenzoic acid tert-butyl ester (143726-85-6) → 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide (95570-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: cuprous chloride / 72 h / Ambient temperature

2: 2.) 85percent m-chloroperbenzoic acid (m-CPBA) / 1.) THF, RT, 18 h, 2.) CH₂Cl₂, RT, 18 h

3: 84 percent / anisole, trifluoroacetic acid (TFA) / 0.5 h / 0 °C

With methoxybenzene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; copper(l) chloride;

DOI:10.1021/jm00171a029

Reference yield:

4-(N,N'-Diisopropyl-carbamimidoyloxymethyl)-benzoic acid tert-butyl ester (128472-99-1) → 4-carboxybenzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene carboxylate 5,5-dioxide (95570-58-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) 85percent m-chloroperbenzoic acid (m-CPBA) / 1.) THF, RT, 18 h, 2.) CH₂Cl₂, RT, 18 h

2: 84 percent / anisole, trifluoroacetic acid (TFA) / 0.5 h / 0 °C

With methoxybenzene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid;

DOI:10.1021/jm00171a029

upstream raw materials:

4-(tert-butoxycarbonyl)benzyl 3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 5,5-dioxide

4-hydroxymethylbenzoic acid tert-butyl ester

4-(N,N'-Diisopropyl-carbamimidoyloxymethyl)-benzoic acid tert-butyl ester

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid