benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

Base Information

• Chemical Name: benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate
• CAS No.: 179034-64-1
• Molecular Formula: C₃₁H₂₆N₄O₄S₃
• Molecular Weight: 614.77
• Mol file: 179034-64-1.mol

Synonyms:benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

Chemical Property of benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

There total 2 articles about benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate 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: 58.0%

benzhydryl (6R,7R)-7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate (92096-37-2) + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (179034-64-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0960-894X(99)00549-1

Reference yield:

(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (54639-48-4) → benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (179034-64-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / K₂CO₃ / dimethylformamide / 1 h / -20 °C

2.1: tBuOK / tetrahydrofuran; 1,2-dimethoxy-ethane / 0.33 h / -10 °C

2.2: 58 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 2 h / -10 - 5 °C

With potassium tert-butylate; potassium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: deprotonation / 2.2: Substitution;

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

Reference yield: 64.0%

benzhydryl 7β-(2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate (179034-64-1) → (6R,7R)-3-(5-Methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (179034-83-4)

Guidance literature:

With methoxybenzene; trifluoroacetic acid; In dichloromethane;

DOI:10.1016/S0960-894X(99)00549-1

upstream raw materials:

benzhydryl (6R,7R)-7β-[(phenylacetyl)amino]-3-[(methylsulfonyl)oxy]-3-cephem-4-carboxylate

2-mercapto-5-methyl-1,3,4-thiadiazole

(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Downstream raw materials:

(6R,7R)-3-(5-Methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

benzhydryl 7β-[2-(2-aminothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate

benzhydryl 7β-[2-(2-formamidothiazol-4-yl)acetamido]-3-(5-methyl-1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate