Reaktion #92324

ord-b4e7473e492f48f7becd710944484f7d

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 38.0%

Edukte

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

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

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

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09447118B2uspto-grants-2016_09