pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

Base Information

Chemical Name:pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate
CAS No.:159296-78-3
Molecular Formula:C₄₄H₄₀N₆O₇S₂
Molecular Weight:828.97
Hs Code.:

Synonyms:pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

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Chemical Property of pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

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Technology Process of pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

There total 7 articles about pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)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: 19.0%

: 53064-79-2
iodomethyl pivaloate

: 159296-68-1
7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylic acid

: 159296-78-3
pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h;
DOI:10.1016/S0968-0896(99)00257-6

Reference yield:

: 500-22-1
3-pyridinecarboxaldehyde

: 159296-78-3
pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 21.0 g / CH₂Cl₂ / 20 h / 20 °C

2.1: 74 percent / conc. HCl / formic acid / 2 h / 20 °C

3.1: Et₃N; trimethylsilyl chloride / tetrahydrofuran / 0.5 h / 20 °C

3.2: 50 percent / tetrahydrofuran; dimethylformamide / 20 °C

4.1: 19 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

With hydrogenchloride; chloro-trimethyl-silane; potassium carbonate; triethylamine; In tetrahydrofuran; formic acid; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 2.1: Hydrolysis / 3.1: silylation / 3.2: Acylation / 4.1: Substitution;
DOI:10.1016/S0968-0896(99)00257-6

Reference yield:

: 143159-43-7
(6R,7R)-7-tert-Butoxycarbonylamino-8-oxo-3-[(triphenyl-λ⁵-phosphanylidene)-methyl]-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 159296-78-3
pivaloyloxymethyl 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-[(Z)-2-(pyridin-3-yl)vinyl]-3-cephem-4-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 21.0 g / CH₂Cl₂ / 20 h / 20 °C

2.1: 74 percent / conc. HCl / formic acid / 2 h / 20 °C

3.1: Et₃N; trimethylsilyl chloride / tetrahydrofuran / 0.5 h / 20 °C

3.2: 50 percent / tetrahydrofuran; dimethylformamide / 20 °C

4.1: 19 percent / K₂CO₃ / dimethylformamide / 0.5 h / 0 °C

With hydrogenchloride; chloro-trimethyl-silane; potassium carbonate; triethylamine; In tetrahydrofuran; formic acid; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 2.1: Hydrolysis / 3.1: silylation / 3.2: Acylation / 4.1: Substitution;
DOI:10.1016/S0968-0896(99)00257-6