diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

Base Information

Chemical Name:diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate
CAS No.:108908-51-6
Molecular Formula:C₃₆H₃₀N₆O₉S₂
Molecular Weight:754.801
Hs Code.:

Synonyms:diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

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Chemical Property of diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

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Technology Process of diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

There total 5 articles about diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-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: 75.4%

: 108908-50-5
diphenylmethyl 7β-<(E)-4-chloro-2-p-nitrobenzyloxycarbonylmethoxyimino-3-oxobutyramido>-3-vinyl-3-cephem-4-carboxylate

: 17356-08-0
thiourea

: 108908-51-6
diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

Guidance literature:: In N,N-dimethyl acetamide; for 12h; Ambient temperature;
DOI:10.1248/cpb.34.3458

Reference yield:

: 108908-46-9
p-nitrobenzyl chloroacetate

: 108908-51-6
diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: 54.5 percent / K₂CO₃ / ethyl acetate; dimethylformamide / 5 h / 50 °C

2: 92.7 percent / TFA / various solvent(s) / 2 h / Ambient temperature

3: 12.7 percent / sulfuryl chloride / acetic acid / 5 h / 50 - 55 °C

4: 1.) POCl₃, DMF; 2.) N-(trimethylsilyl)acetamide / 1.) EtOAc, 0-5 deg C, 30 min; 2.) THF, -20- -30 deg C, 30 min

5: 75.4 percent / N,N-dimethyl-acetamide / 12 h / Ambient temperature

With sulfuryl dichloride; potassium carbonate; N,N-dimethyl-formamide; N-Trimethylsilylacetamide; trifluoroacetic acid; trichlorophosphate; In N,N-dimethyl acetamide; acetic acid; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1248/cpb.34.3458

Reference yield:

: 108908-48-1
(Z)-2-p-nitrobenzyloxycarbonylmethoxyimino-3-oxobutyric acid

: 108908-51-6
diphenylmethyl 7β-<(E)-2-(2-amino-4-thiazolyl)-2-p-nitrobenzyloxycarbonylmethoxyiminoacetamido>-3-vinyl-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: 12.7 percent / sulfuryl chloride / acetic acid / 5 h / 50 - 55 °C

2: 1.) POCl₃, DMF; 2.) N-(trimethylsilyl)acetamide / 1.) EtOAc, 0-5 deg C, 30 min; 2.) THF, -20- -30 deg C, 30 min

3: 75.4 percent / N,N-dimethyl-acetamide / 12 h / Ambient temperature

With sulfuryl dichloride; N,N-dimethyl-formamide; N-Trimethylsilylacetamide; trichlorophosphate; In N,N-dimethyl acetamide; acetic acid;
DOI:10.1248/cpb.34.3458