2-Propanesulfonyl chloride → HCID 86607903, compound

Participants

Reaction Steps

To a solution of 0.15 g (0.28 mmol) of (3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (Example 47, Step 8) in CH2Cl2 (1.3 mL) was added 3 mL of saturated sodium bicarbonate followed by isopropylsulfonyl chloride (0.1 mL, 0.9 mmol). The reaction mixture was stirred overnight, taken up in ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica chromatography (silica pre-washed with methanol) eluting with a gradient of 1-5% MeOH/CH2Cl2 to afford (3S,4R)-N-tert-butoxy-1-(isopropylsulfonyl)-3-methyl-4-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]piperidine-3-carboxamide (0.12 g, 66%) as a colorless solid. MS: 647.2 (M+H)+

Provenance & Evidence