Hydrochloric Acid → 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid

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To a solution of ethyl 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (40.0 mg, 0.093 mmol) in THF (1.1 ml), MeOH (372 μl), and Water (372 μl) at 0° C., was added lithium hydroxide (5.2 mg, 0.217 mmol). The mixture was stirred for 1 hour. This mixture was left standing over the course of 2 days at room temperature. To this mixture, was added HCl (214 μl, 0.214 mmol), then, the mixture was concentrated under vacuum, diluted in dichloromethane (50 ml) and washed with water (20 ml×3). The organic layer was dried, filtered, and evaporated to give 2-(2-cyano-3,5-dimethyl-4-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid as a solid. 1H NMR (CDCl3/400 MHz) δ (ppm) 7.95-7.90 (m, 1H), 7.43-7.37 (m, 1H), 7.34-7.28 (m, 1H), 6.92-6.86 (m, 1H), 4.77 (s, 2H), 4.19 (s, 2H), 3.44-3.33 (m, 4H), 2.07 (s, 3H), 2.02 (s, 3H), 1.98-1.93 (m, 4H). MS m/z: 402.3 (M+1).

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