(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester
• CAS No.: 186503-37-7
• Molecular Formula: C₂₄H₂₃NO₈S
• Molecular Weight: 485.515

Synonyms:(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

Chemical Property of (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

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Technology Process of (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

There total 4 articles about (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl 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: 90.0%

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester (186503-36-6) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester (186503-37-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; for 2h; Ambient temperature;

DOI:10.1055/s-1998-1620

Reference yield:

3-deacetyloxy-7-aminocephalosporanic acid (22252-43-3,26395-99-3,70287-30-8,72059-35-9) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester (186503-37-7)

Guidance literature:

Multi-step reaction with 4 steps

1: CH₃SO₃H, NaNO₂ / 21 h / Ambient temperature

2: NaHCO₃, NaBr / dimethylformamide / 18 h / Ambient temperature

3: 75 percent / LDA / tetrahydrofuran / 1.) -70 deg C, 30 min, 2.) -70 deg C, 90 min

4: 90 percent / MCPBA / ethyl acetate / 2 h / Ambient temperature

With methanesulfonic acid; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bromide; lithium diisopropyl amide; sodium nitrite; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1998-1620

Reference yield:

7α-Methoxy-3-methyl-3-cephem-4-carboxylic acid (126621-86-1) → (6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5,8-trioxo-5λ6-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester (186503-37-7)

Guidance literature:

Multi-step reaction with 3 steps

1: NaHCO₃, NaBr / dimethylformamide / 18 h / Ambient temperature

2: 75 percent / LDA / tetrahydrofuran / 1.) -70 deg C, 30 min, 2.) -70 deg C, 90 min

3: 90 percent / MCPBA / ethyl acetate / 2 h / Ambient temperature

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; sodium bromide; lithium diisopropyl amide; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1055/s-1998-1620

upstream raw materials:

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid 4-methoxy-benzyl ester

3-deacetyloxy-7-aminocephalosporanic acid

7α-Methoxy-3-methyl-3-cephem-4-carboxylic acid

(6R,7S)-7-Methoxy-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

Downstream raw materials:

(6R,7S)-2-Benzoyl-7-methoxy-3-methyl-5,5-dioxo-5λ⁶-thia-1-aza-bicyclo[4.2.0]oct-2-en-8-one

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