(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

Base Information

Chemical Name:(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester
CAS No.:189449-58-9
Molecular Formula:C₅₇H₅₂ClN₇O₇S₄
Molecular Weight:1110.8
Hs Code.:

(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

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Chemical Property of (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

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Technology Process of (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

There total 10 articles about (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester 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: 26.0%

: 189449-57-8
3-(N-tert-butoxycarbonylaminoethylsulfenylmethyl)-4-chloropyridine

: 189449-55-6
(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-mercapto-3-cephem-4-carboxylate diphenylmethyl ester

: 189449-58-9
(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

Guidance literature:: In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.7164/antibiotics.53.1272

Reference yield:

: 626-61-9
4-Chloropyridine

: 189449-58-9
(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: LDA

2: 84 percent / SOCl₂ / dimethylformamide / 0.75 h

3: 96 percent / NaI; diisopropylethylamine / dimethylformamide / 2 h / 20 °C

4: 26 percent / dimethylformamide / 20 °C

With thionyl chloride; N-ethyl-N,N-diisopropylamine; sodium iodide; lithium diisopropyl amide; In N,N-dimethyl-formamide;
DOI:10.7164/antibiotics.53.1272

Reference yield:

: 76-83-5
trityl chloride

: 189449-58-9
(7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino)acetamido]-3-[3-(N-tert-butoxycarbonylaminoethylthiomethyl)pyrid-4-ylthio]-3-cephem-4-carboxylate diphenylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: T-BuOK / tetrahydrofuran

2: KOH / ethanol / Saponification

3: 71 percent / N-chlorosuccinimide / dimethylformamide / 20 °C

4: 65 percent / pyridine; POCl₃ / tetrahydrofuran / 0.5 h / cooling

5: 95 percent / sodium hydrogen sulfide hydrate / dimethylformamide / 0.25 h / -20 °C

6: 26 percent / dimethylformamide / 20 °C

With pyridine; potassium hydroxide; N-chloro-succinimide; sodium hydrogensulfide; potassium tert-butylate; trichlorophosphate; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide;
DOI:10.7164/antibiotics.53.1272