(6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 132261-11-1
• Molecular Formula: C₂₅H₂₆N₄O₃S₂
• Molecular Weight: 494.638

Synonyms:(6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

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Technology Process of (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 2 articles about (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-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:

diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate (52681-36-4) → (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (132261-11-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / Cu₂O / tetrahydrofuran / 3.5 h / 45 °C

2: Br₂ / toluene; CCl₄ / -78 - 20 °C

3: tetrahydrofuran / 1 h / -78 °C

With copper(I) oxide; bromine; In tetrahydrofuran; tetrachloromethane; toluene;

DOI:10.1021/jm00107a035

Reference yield:

C23H20Br2N2O3S2 (133655-82-0) + ethylenediamine (107-15-3,85404-18-8) → (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (132261-11-1)

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1021/jm00107a035

Reference yield:

methanol (67-56-1) + (6R,7S)-7-(4,5-Dihydro-1H-imidazol-2-ylamino)-3-methyl-7-methylsulfanyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (132261-11-1) → diphenylmethyl 7-(imidazol-2-ylamino)-7-methoxy-3-methylceph-3-em-4-carboxylate (132261-12-2)

Guidance literature:

With pyridine; mercury dichloride; In dichloromethane; N,N-dimethyl-formamide; at -15 - 0 ℃;

DOI:10.1021/jm00107a035

upstream raw materials:

C₂₃H₂₀Br₂N₂O₃S₂

ethylenediamine

diphenylmethyl (6R,7R)-7-isocyano-3-methylceph-3-em-4-carboxylate

Downstream raw materials:

diphenylmethyl 7-(imidazol-2-ylamino)-7-methoxy-3-methylceph-3-em-4-carboxylate

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