Reacción #92324

ord-b4e7473e492f48f7becd710944484f7d

Ecuación de reacción

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
Rendimiento 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
Rendimiento 38.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

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

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09447118B2uspto-grants-2016_09