Реакция #92324

ord-b4e7473e492f48f7becd710944484f7d

Уравнение реакции

CN(C)C(=O)[C@H]1CC[C@@H](O)[C@H](NS(=O)(=O)NC(=O)OC(C)(C)C)C1
t-Butyl {[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]sulfamoyl}carbamate
Cc1ccc(S(=O)(=O)Cl)cc1
p-toluenesulfonyl chloride
Cn1ccnc1
N-methylimidazole
Cc1ccc(S(=O)(=O)O[C@@H]2CC[C@H](C(=O)N(C)C)C[C@H]2NS(=O)(=O)NC(=O)OC(C)(C)C)cc1
title compound
Выход 38.0%
Cc1ccc(S(=O)(=O)O[C@@H]2CC[C@H](C(=O)N(C)C)C[C@H]2NS(=O)(=O)NC(=O)OC(C)(C)C)cc1
(1R,2R,4S)-2-{[(t-Butoxycarbonyl) sulfamoyl]amino}-4-(dimethylcarbamoyl)cyclohexyl 4-methylbenzenesulfonate
Выход 38.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ДругоеThereafter, the reaction mixture was purified by silica gel column chromatography

Методика

t-Butyl {[(1R,2R,5S)-5-(dimethylcarbamoyl)-2-hydroxycyclohexyl]sulfamoyl}carbamate (200 mg) was dissolved in dichloromethane (2.0 mL), and p-toluenesulfonyl chloride (136 mg) and N-methylimidazole (87.0 mL) were then added to the obtained solution. The obtained mixture was stirred at room temperature for approximately 20 hours. Thereafter, the reaction mixture was purified by silica gel column chromatography to obtain the title compound (107 mg, yield: 38%) in the form of powder.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09447118B2uspto-grants-2016_09