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

Base Information

• Chemical Name: diphenylmethyl 7β-[(Z)-2-(5-fluoro-2-formylaminothiazol-4-yl)-2-(formyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate
• CAS No.: 189099-21-6
• Molecular Formula: C₅₀H₃₈FN₇O₇S₃
• Molecular Weight: 964.091

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

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

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

There total 3 articles about diphenylmethyl 7β-[(Z)-2-(5-fluoro-2-formylaminothiazol-4-yl)-2-(formyloxyimino)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: 46.0%

diphenylmethyl 7β-amino-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (189099-17-0) + diphenylmethyl 7β-[(Z)-2-(2-formamidothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (454472-38-9) → diphenylmethyl 7β-[(Z)-2-(5-fluoro-2-formylaminothiazol-4-yl)-2-(formyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (189099-21-6)

Guidance literature:

diphenylmethyl 7β-[(Z)-2-(2-formamidothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate; With N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; at 0 ℃; for 1h;

diphenylmethyl 7β-amino-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate; With benzenesulfonamide; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃;

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-fluoro-2-formylaminothiazol-4-yl)-2-(formyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (189099-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaSH; i-Pr₂NEt / dimethylformamide / 1 h / -20 °C

1.2: 56 percent / dimethylformamide / 1 h / -5 °C

2.1: POCl₃; DMF / tetrahydrofuran / 1 h / 0 °C

2.2: 46 percent / BSA / dimethylformamide; tetrahydrofuran / 0 °C

With sodium hydrogensulfide; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

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

Reference yield:

4-chloromethyl-1-tritylpyrazole → diphenylmethyl 7β-[(Z)-2-(5-fluoro-2-formylaminothiazol-4-yl)-2-(formyloxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate (189099-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaSH; i-Pr₂NEt / dimethylformamide / 1 h / -20 °C

1.2: 56 percent / dimethylformamide / 1 h / -5 °C

2.1: POCl₃; DMF / tetrahydrofuran / 1 h / 0 °C

2.2: 46 percent / BSA / dimethylformamide; tetrahydrofuran / 0 °C

With sodium hydrogensulfide; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

diphenylmethyl 7β-amino-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

diphenylmethyl 7β-[(Z)-2-(2-formamidothiazol-4-yl)-2-(1-tert-butoxycarbonyl-1-methylethoxyimino)acetamido]-3-[(1-tritylpyrazol-4-yl)methylthio]-3-cephem-4-carboxylate

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

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