Benzenesulfonyl chloride → HCID 131733393, compound

Participants

Reaction Steps

To a ice-cooled solution of (S)-1-(4-amino-2-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)phenyl)-N,N-dibutyl-5-methyl-1H-pyrazole-3-carboxamide (intermediate B, 0.20 g, 0.316 mmol) in DCM (2 mL) was added Et3N (0.05 mL, 0.47 mmol) and benzenesulfonyl chloride (0.06 g, 0.38 mmol) followed by stirring at RT for 16 h. The reaction mixture was diluted with water (20 mL) and extracted with EtOAc (100 mL). The organic layer was washed with brine (50 mL), dried over sodium sulphate and concentrated invacuo. The residue was purified on silica gel (100-200 mesh) to afford (S)—N,N-dibutyl-1-(2-(3-(((tert-butyldimethylsilyl)oxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(phenylsulfonamido)phenyl)-5-methyl-1H-pyrazole-3-carboxamide as a mixture of mono and bis sulfonamides, 0.21 g (crude). The crude reaction mass was used in the next reaction without further purification. Rf=0.75 (50% EtOAc in hexane); ES-MS: m/z 772.6 (M+H).

Provenance & Evidence