(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

Chemical Name:(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
CAS No.:258497-39-1
Molecular Formula:C₅₇H₅₂ClN₇O₇S₄
Molecular Weight:1110.8
Hs Code.:

(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Chemical Property of (7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Technology Process of (7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 7 articles about (7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl 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: 33.0%

: 258497-38-0
[2-(3-mercapto-pyridin-4-ylmethylsulfanyl)-ethyl]-carbamic acid tert-butyl ester

: (7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-methanesulfonyloxy-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

: 258497-39-1
(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: In ethyl acetate; at 20 ℃; for 1h;
DOI:10.1016/S0968-0896(02)00431-5

Reference yield:

: 67385-09-5
2-[(tert-butoxycarbonyl)amino]-1-ethanethiol

: 258497-39-1
(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: DMF; thionyl chloride / 0.5 h / 20 °C

1.2: 58 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C

2.1: triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

2.2: 79 percent / diisopropylethylamine / tetrahydrofuran / 3 h / 20 °C

3.1: 96 percent / NaOMe / methanol / 0.5 h / 50 °C

4.1: 33 percent / ethyl acetate / 1 h / 20 °C

With triethylsilane; thionyl chloride; sodium methylate; N,N-dimethyl-formamide; trifluoroacetic acid; In methanol; dichloromethane; ethyl acetate;
DOI:10.1016/S0968-0896(02)00431-5

Reference yield:

: 18103-75-8
3-mercaptoisonicotinic acid

: 258497-39-1
(7R,6R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-(Z)-trityloxyimino-acetylamino]-3-[4-(2-tert-butoxycarbonylaminoethylsulfanylmethyl)-pyridin-3-ylsulfanyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: borane / tetrahydrofuran / 0.5 h

2.1: 67 mg / diisopropylethylamine / dimethylformamide / 0.5 h

3.1: DMF; thionyl chloride / 0.5 h / 20 °C

3.2: 58 percent / potassium carbonate / dimethylformamide / 0.5 h / 20 °C

4.1: triethylsilane; trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

4.2: 79 percent / diisopropylethylamine / tetrahydrofuran / 3 h / 20 °C

5.1: 96 percent / NaOMe / methanol / 0.5 h / 50 °C

6.1: 33 percent / ethyl acetate / 1 h / 20 °C

With triethylsilane; thionyl chloride; borane; sodium methylate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(02)00431-5