Reaktion #1870598

Reaktionsgleichung

5-chloropyridine-2-sulfonyl chloride

[(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester

HCl 1,4-dioxan

Hünig's base

→

5-Chloro-pyridine-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide

Lösungsmittel

CH2Cl2

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto react for 1 h
2. 2
   EinengenThe reaction mixture was concentrated under reduced pressure
3. 3
   Einengenconcentrated once from acetonitrile
4. 4
   workup.ADDITIONTo the resultant hydrochloride salt was added CH2Cl2 (15 ml)
5. 5
   SonstigeThe reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100)

Vorschrift

[(R)-1-(2,4-Dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (0.46 g, 1.0 mmol) was dissolved in 20 ml dichloromethane. 4 M HCl/1,4-dioxan (20 ml) were added dropwise and the mixture was allowed to react for 1 h. The reaction mixture was concentrated under reduced pressure and concentrated once from acetonitrile. To the resultant hydrochloride salt was added CH2Cl2 (15 ml) followed by the dropwise addition of Hünig's base (0.44 ml, 2.5 mmol). A solution of 5-chloropyridine-2-sulfonyl chloride (0.33 g, 1.1 mmol) in CH2Cl2 (5 ml) was added and the reaction mixture (pH 8) was stirred for a further 1.5 h. The reaction mixture was purified over silica gel (heptane-ethylacetate, 95:5-0:100): white solid 0.37 g (76%);

Quelle