(6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 179034-90-3
• Molecular Formula: C₂₈H₂₃N₇O₅S₃
• Molecular Weight: 633.733

Synonyms:

Chemical Property of (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

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Useful:

Technology Process of (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 4 articles about (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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:

[2-(formylamino)-1,3-thiazol-4-yl]acetyl chloride (782441-52-5) + benzhydryl 7β-amino-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate (179034-53-8) → (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (179034-90-3)

Guidance literature:

With N-Trimethylsilylacetamide; In tetrahydrofuran; dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/S0968-0896(00)00163-2

Reference yield:

diphenylmethyl 7β-formamido-3-methanesulfonyloxy-3-cephem-4-carboxylate → (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (179034-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 52 percent / N,N-diisopropylethylamine / dimethylformamide / 4 h

2: 15 percent / HCl / methanol; H₂O; tetrahydrofuran / 1.5 h / 20 °C

3: N-trimethylsilylacetamide / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

With hydrogenchloride; N-ethyl-N,N-diisopropylamine; N-Trimethylsilylacetamide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 1: Substitution / 2: Hydrolysis / 3: Acylation;

DOI:10.1016/S0968-0896(00)00163-2

Reference yield:

[2-(formylamino)-1,3-thiazol-4-yl]acetic acid (75890-68-5) → (6R,7R)-7-[2-(2-Formylamino-thiazol-4-yl)-acetylamino]-8-oxo-3-(4H-[1,2,4]triazol-3-ylsulfanyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (179034-90-3)

Guidance literature:

Multi-step reaction with 2 steps

1: PCl₅ / CH₂Cl₂ / 0.5 h / 0 °C

2: N-trimethylsilylacetamide / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

With phosphorus pentachloride; N-Trimethylsilylacetamide; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Acylation;

DOI:10.1016/S0968-0896(00)00163-2

upstream raw materials:

[2-(formylamino)-1,3-thiazol-4-yl]acetyl chloride

benzhydryl 7β-amino-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate

[2-(formylamino)-1,3-thiazol-4-yl]acetic acid

benzhydryl 7β-formamido-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate

Downstream raw materials:

benzhydryl 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-(1,2,4-triazol-3-yl)thio-3-cephem-4-carboxylate

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