4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride → methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate

Participants

Reaction Steps

To a solution of methyl (1R,2R)-2-amino-1-hydroxycyclopentanecarboxylate (2.1 mmol) in CH2Cl2 (8 mL) and saturated sodium bicarbonate (8 mL) was added 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (0.88 g, 1.1 eq). The reaction was allowed to stir for 18 h at room temperature, and then taken up in ethyl acetate, washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified using ilica chromatography eluting with a gradient of 50% -70% ethyl acetate/hexanes afforded methyl (1R,2R)-1-hydroxy-2-[({4-[(2-methylquinolin-4-yl)methoxy]phenyl}sulfonyl)amino]cyclopentanecarboxylate (0.2 g, 20%). MS: 470.1 (M+H)+

Provenance & Evidence