diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Base Information

• Chemical Name: diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate
• CAS No.: 454472-45-8
• Molecular Formula: C₅₂H₄₄N₈O₅S₃
• Molecular Weight: 957.17
• Mol file: 454472-45-8.mol

Synonyms:diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Chemical Property of diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

There total 3 articles about diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-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: 39.0%

4-benzoylthiomethyl-1-(trityl)pyrazole (163008-91-1) + diphenylmethyl 7β-[(Z)-2-(5-aminothiadiazol-3-yl)-2-(3-cyclopentenyloxyimino)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate (454472-33-4) → diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (454472-45-8)

Guidance literature:

4-benzoylthiomethyl-1-(trityl)pyrazole; With sodium methylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; at 0 ℃; for 1h;

diphenylmethyl 7β-[(Z)-2-(5-aminothiadiazol-3-yl)-2-(3-cyclopentenyloxyimino)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; at -65 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00416-3

Reference yield:

diphenylmethyl 7β-amino-3-methanesulfonyloxy-3-cephem-4-carboxylate (74704-03-3) → diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (454472-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / BSA / CH₂Cl₂ / 5 - 20 °C

2.1: MeONa / tetrahydrofuran; dimethylformamide; methanol / 1 h / 0 °C

2.2: 39 percent / tetrahydrofuran; dimethylformamide; methanol / 1 h / -65 °C

With benzenesulfonamide; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00416-3

Reference yield:

(5-Amino-[1,2,4]thiadiazol-3-yl)-[(Z)-cyclopent-2-enyloxyimino]-acetyl chloride; hydrochloride → diphenylmethyl 7β-[(Z)-2-(5-aminothiadizol-3-yl)-2-(cyclopentenyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (454472-45-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 74 percent / BSA / CH₂Cl₂ / 5 - 20 °C

2.1: MeONa / tetrahydrofuran; dimethylformamide; methanol / 1 h / 0 °C

2.2: 39 percent / tetrahydrofuran; dimethylformamide; methanol / 1 h / -65 °C

With benzenesulfonamide; sodium methylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00416-3

upstream raw materials:

4-benzoylthiomethyl-1-(trityl)pyrazole

diphenylmethyl 7β-[(Z)-2-(5-aminothiadiazol-3-yl)-2-(3-cyclopentenyloxyimino)acetamido]-3-methanesulfonyloxy-3-cephem-4-carboxylate

diphenylmethyl 7β-amino-3-methanesulfonyloxy-3-cephem-4-carboxylate