Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Base Information

• Chemical Name: Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester
• CAS No.: 104163-99-7
• Molecular Formula: C₁₈H₂₀N₂O₇S
• Molecular Weight: 408.432

Synonyms:Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Chemical Property of Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

Chemical Property:

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Technology Process of Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

There total 5 articles about Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl 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: 28.0%

Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester (128472-69-5) → Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester (104163-99-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 18h; Ambient temperature;

DOI:10.1021/jm00171a029

Reference yield:

3-(acetoxymethyl)-7α-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (95570-59-5) → Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester (104163-99-7)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / acetone; dioxane / 0.5 h / -20 °C

2: acetone; dioxane; H₂O / 2 h

3: 28 percent / m-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 18 h / Ambient temperature

With pyridine; 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1021/jm00171a029

Reference yield:

Acetic acid (6R,7S)-2-isobutoxycarbonyloxycarbonyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester → Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester (104163-99-7)

Guidance literature:

Multi-step reaction with 2 steps

1: acetone; dioxane; H₂O / 2 h

2: 28 percent / m-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 18 h / Ambient temperature

With 3-chloro-benzenecarboperoxoic acid; In 1,4-dioxane; dichloromethane; water; acetone;

DOI:10.1021/jm00171a029

upstream raw materials:

Acetic acid (6R,7S)-2-benzylcarbamoyl-7-methoxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-en-3-ylmethyl ester

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

t-butyl 3-acetoxymethyl-7α-methoxy-3-cephem-4-carboxylate

7-Aminocephalosporanic acid

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