Dimethylformamide → 2-Propen-1-yl (5-(6-isoquinolinyl)-3-isoxazolyl)((2S)-2-methyl-3-(4-(trifluoromethyl)phenyl)propyl)carbamate

Participants

Reaction Steps

To a solution of allyl 5-(isoquinolin-6-yl)isoxazol-3-ylcarbamate (0.030 g, 0.10 mmol) in 1 mL of DMF was added sodium hydride (0.0049 g, 0.20 mmol). After 15 minutes, (S)-tert-butyl 4-(4-(trifluoromethyl)benzyl)-1,2,3-oxathiazolidine-3-carboxylate-2,2-dioxide (0.077 g, 0.20 mmol) (prepared as shown in Scheme 1) was added. The mixture was stirred for 30 minutes. The solvent was removed under reduced pressure and the residue was taken up in 5 mL of EtOAc. 5 mL of 10% aq. HCl was then added and the mixture was stirred for 1 hour. A precipitate formed during this period. 10 mL of 5% aqueous NaOH was then added to solubilize the precipitate and the biphasic mixture was partitioned in a separatory funnel. The aqueous portion was extracted three times with 5 mL of EtOAc. The combined organic extracts were washed with 5 mL of brine and dried over MgSO4. Filtration and concentration under reduced pressure, followed by flash chromatography on silica gel (10% to 50% EtOAc/hexanes) afforded the desired adduct (0.031 g, 51% yield) as a white solid.

Provenance & Evidence