(6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 62543-30-0
• Molecular Formula: C₃₂H₂₉N₅O₇S₃
• Molecular Weight: 691.81

Synonyms:

Chemical Property of (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property:

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Useful:

Technology Process of (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 6 articles about (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-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-sulpho-2-phenylacetyl chloride (40125-73-3) + benzhydryl 7-amino-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)ceph-3-em-4-carboxylate (62543-15-1) → (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (62543-30-0)

Guidance literature:

With N,N-dimethyl-aniline; In dichloromethane; at 2 ℃; for 0.5h;

DOI:10.1248/cpb.28.2116

Reference yield:

benzhydryl 3-formyl-7-thienylacetamidoceph-3-em-4-carboxylate (33741-82-1) → (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (62543-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / dimethylsulfoxide / 0.5 h / Ambient temperature

2: 90 percent / DDQ / dioxane / 0.17 h / Ambient temperature; further reag., and time

3: 1.) pyridine, phosphorus pentachloride; 2.) methanol / 1.) CH₂Cl₂, 10 deg C, 1 h; 2.) -20 deg C, 2 h

4: N,N-dimethylaniline / CH₂Cl₂ / 0.5 h / 2 °C

With pyridine; methanol; phosphorus pentachloride; N,N-dimethyl-aniline; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; dichloromethane; dimethyl sulfoxide;

DOI:10.1248/cpb.28.2116

Reference yield:

benzhydryl 3-(4,4-dimethylaminothiocarbonylhydrazonomethyl)-7-thienylacetamidoceph-3-em-4-carboxylate (62543-12-8) → (6R,7R)-3-(5-Dimethylamino-[1,3,4]thiadiazol-2-yl)-8-oxo-7-(2-phenyl-2-sulfo-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (62543-30-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DDQ / dioxane / 0.17 h / Ambient temperature; further reag., and time

2: 1.) pyridine, phosphorus pentachloride; 2.) methanol / 1.) CH₂Cl₂, 10 deg C, 1 h; 2.) -20 deg C, 2 h

3: N,N-dimethylaniline / CH₂Cl₂ / 0.5 h / 2 °C

With pyridine; methanol; phosphorus pentachloride; N,N-dimethyl-aniline; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,4-dioxane; dichloromethane;

DOI:10.1248/cpb.28.2116

upstream raw materials:

2-sulpho-2-phenylacetyl chloride

benzhydryl 7-amino-3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)ceph-3-em-4-carboxylate

benzhydryl 3-formyl-7-thienylacetamidoceph-3-em-4-carboxylate

benzhydryl 3-(5-dimethylamino-1,3,4-thiadiazol-2-yl)-7-thienylacetamidoceph-3-em-4-carboxylate

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