(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
CAS No.:331780-41-7
Molecular Formula:C₃₄H₃₁ClN₆O₅S₂
Molecular Weight:703.242
Hs Code.:

(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

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Chemical Property of (6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

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Technology Process of (6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 3 articles about (6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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: 14.1%

: 331780-40-6
(7R,6R)-7-amino-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

: (5-amino-[1,2,4]thiadiazol-3-yl)-(Z)-trityloxyimino-acetic acid methyl ester sodium salt

: 331780-41-7
(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Guidance literature:: (5-amino-[1,2,4]thiadiazol-3-yl)-(Z)-trityloxyimino-acetic acid methyl ester sodium salt; With chlorophosphoric acid diphenyl ester; In tetrahydrofuran; at 20 ℃; for 1h;

(7R,6R)-7-amino-3-chloro-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester; With 2,6-dimethylpyridine; In tetrahydrofuran; at 20 ℃; for 3h;
DOI:10.1016/S0968-0896(02)00431-5

Reference yield:

: 53994-69-7
(6R,7R)-1-aza-3-chloro-7-amino-8-oxo-5-thiabicyclo<4.2.0>oct-2-ene-2-carboxylic acid

: 331780-41-7
(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 52 percent / BF₃*Et₂O / 20 °C

2.1: diphenylchlorophosphonate / tetrahydrofuran / 1 h / 20 °C

2.2: 14.1 percent / 2,6-lutidine / tetrahydrofuran / 3 h / 20 °C

With boron trifluoride diethyl etherate; chlorophosphoric acid diphenyl ester; In tetrahydrofuran;
DOI:10.1016/S0968-0896(02)00431-5

Reference yield:

: 620967-17-1
(5-methoxycarbonylamino-[1,2,4]thiadiazol-3-yl)-(Z)-trityloxyimino-acetic acid methyl ester

: 331780-41-7
(6R,7R)-7-[2-(5-amino-[1,2,4]thiadiazol-3-yl)-2-(Z)-trityloxyimino-acetylamino]-3-chloro-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 70 percent / NaOH / ethanol; H₂O / 8 h / Heating

2.1: diphenylchlorophosphonate / tetrahydrofuran / 1 h / 20 °C

2.2: 14.1 percent / 2,6-lutidine / tetrahydrofuran / 3 h / 20 °C

With sodium hydroxide; chlorophosphoric acid diphenyl ester; In tetrahydrofuran; ethanol; water;
DOI:10.1016/S0968-0896(02)00431-5