Water → HCID 11991560, compound

Reaction equation

CC1C=CC(S(O[CH2:12][CH2:13][N:14]([CH2:25][C@H:26]([OH:28])[CH3:27])[S:15]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=2)(=[O:17])=[O:16])(=O)=O)=CC=1.[H-].[Na+].O>C1COCC1>[CH3:27][C@H:26]1[O:28][CH2:12][CH2:13][N:14]([S:15]([C:18]2[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=2)(=[O:16])=[O:17])[CH2:25]1

Participants

Procedure

To a solution of 2-{[(2R)-2-hydroxypropyl][(4-methylphenyl)sulfonyl]amino}ethyl 4-methylbenzenesulfonate (340 g, 0.80 mol) in dry THF (3 L) at 0° C. was added NaH (60%, 120 g, 3.00 mol) portion wise. The reaction mixture was warmed to room temperature and stirred for 14 h. The reaction was then cooled to 0° C., and water (100 mL) was added to quench the reaction. The mixture was completely quenched by pouring into water (1 L) and the phases were separated. The aqueous phase was extracted with EtOAc (3×500 mL) and the combined organic layers were washed with brine (500 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel chromatography (8:1 petroleum ether:EtOAc) to yield the title compound as an oil.