Reaktion #2285453

Reaktionsgleichung

2-oxaadamantane-1-carbonylchloride

triethylamine

2-Amino-4-(methylsulfonyl)benzoic acid

3,3-difluoro-azetidine hydrochloride

→

title compound

N-[2-[(3,3-difluoroazetidin-1-yl)carbonyl]-5-(methylsulfonyl)phenyl]-2-oxatricyclo[3.3.1.13,7]decane-1-carboxamide

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeEvaporation of solvents and flash chromotography over silica gel (10% ethyl acetate/hexane)

Vorschrift

2-Amino-4-(methylsulfonyl)benzoic acid (0.25 g) and 3,3-difluoro-azetidine hydrochloride (0.19 g) were reacted according to the method described in Example 332C. The resultant intermediate (0.14 g) was then reacted with 2-oxaadamantane-1-carbonylchloride (1.25 equiv) (prepared from 2-oxaadamantane-1-carboxylic acid and thionyl chloride as in Example 12) and triethylamine (2 equiv) in acetonitrile (10 mL). Evaporation of solvents and flash chromotography over silica gel (10% ethyl acetate/hexane) provided 110 mg of the title compound. 1H NMR (dimethylsulfoxide-d6, 300 MHz) δ 1.66-2.03 (m, 10H), 2.19 (br s, 2H), 3.25 (s, 3H), 4.43-4.57 (br, 2H), 4.63-4.70 (br, 2H), 7.66 (dd, 1H), 7.82 (d, 1H), 8.79 (d, 1H), 10.76 (s, 1H); MS (ESI+) m/z 455 (M+H)+.

Quelle