(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

Base Information

Chemical Name:(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate
CAS No.:308121-49-5
Molecular Formula:C₂₉H₂₂N₄O₄S₄
Molecular Weight:618.782
Hs Code.:

Synonyms:(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

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Chemical Property of (E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

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Technology Process of (E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

There total 5 articles about (E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-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: 59.0%

: 119924-22-0
(E)-3-(thien-3-yl)acryloyl chloride

: benzhydryl 7β-amino-3-(1,3,4-thiadiazol-2-yl)thio-3-cephem-4-carboxylate hydrochloride

: 308121-49-5
(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

Guidance literature:: With N-Trimethylsilylacetamide; In tetrahydrofuran; dichloromethane; at 0 ℃; for 1h;
DOI:10.1016/S0968-0896(00)00163-2

Reference yield:

: 1195-52-4,102696-71-9
trans-3-(3-thienyl)acrylic acid

: 308121-49-5
(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: PCl₅ / CH₂Cl₂ / 0.5 h / 0 °C

2: 59 percent / N-trimethylsilylacetamide / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

With phosphorus pentachloride; N-Trimethylsilylacetamide; In tetrahydrofuran; dichloromethane; 1: Substitution / 2: Acylation;
DOI:10.1016/S0968-0896(00)00163-2

Reference yield:

: 54639-48-4
(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

: 308121-49-5
(E)-benzhydryl 7β-[3-(3-thienyl)acryloylamino]-3-(1,3,4-thiadiasol-2-yl)thio-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 4 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: 40 percent / tetrahydrofuran; 1,2-dimethoxy-ethane / 2 h / -10 - 5 °C

3.1: 64 percent / PCl₅; Py / CH₂Cl₂ / 1.5 h / -10 - -5 °C

4.1: 59 percent / N-trimethylsilylacetamide / tetrahydrofuran; CH₂Cl₂ / 1 h / 0 °C

With pyridine; phosphorus pentachloride; potassium tert-butylate; potassium carbonate; N-Trimethylsilylacetamide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: deprotonation / 2.2: Substitution / 3.1: Substitution / 4.1: Acylation;
DOI:10.1016/S0968-0896(00)00163-2