Sodium Hydroxide → HCID 53246859, compound

Participants

Reaction Steps

To a stirring solution of ethyl 2-(2,5-dimethyl-3-phenyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (0.029 g, 0.060 mmol) in tetrahydrofuran (1 ml) and water (1 ml) was added 1N sodium hydroxide (0.121 ml, 0.121 mmol). Upon addition, the reaction changed color from pink to yellow. The mixture was stirred overnight, after which LCMS analysis indicated reaction completion. The reaction was quenched with 0.050 ml of 3N HCl and stirred to afford a pink color. The crude mixture was concentrated and taken up in acetonitrile and purified by reverse phase HPLC chromatography. Acetonitrile and water spiked with 0.1% TFA were used as eluents. The desired fractions were collected and quenched with aqueous saturated sodium bicarbonate solution and washed with ether. The aqueous layer was then acidified with 3N HCl to pH=1 and this aqueous layer was extracted 3 times with ether. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to afford a purple solid (0.0203 g, 0.045 mmol, 74.3% yield). 1H NMR (CDCl3/400 MHz)ppm) 7.91 (d, 1H), 7.37-7.33 (m, 1H), 7.23-7.17 (m, 1H), 7.15-7.11 (m, 3H), 7.08-7.05 (m, 1H), 6.99-6.97 (m, 2H), 4.63 (s, 2H), 4.07 (s, 2H), 3.08-3.04 (m, 4H), 2.14 (s, 3H), 1.98 (s, 3H), 1.61-1.58 (m, 4H). LCMS (M+1): 453.3.

Provenance & Evidence