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

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Reaction Steps

To a solution of ethyl 2-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (286.9 mg, 0.668 mmol) in THF (8.0 ml), MeOH (2.7 ml), and water (2.7 ml) at 0° C., was added lithium hydroxide (32.0 mg, 1.336 mmol). The mixture was stirred for 1 hour. To this mixture, was then added HCl (1336 μl, 1.336 mmol) and the resulting mixture 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-(3-cyano-2,4-dimethyl-5-(2-(pyrrolidin-1-ylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (290.0 mg, 0.722 mmol, 108% yield) as a solid. 1H NMR (CDCl3/400 MHz) δ (ppm) 9.52 (bs, 1H), 7.87-7.82 (m, 1H), 7.42-7.35 (m, 1H), 7.34-7.28 (m, 1H), 6.92-6.86 (m, 1H), 4.33 (s, 2H), 4.25 (s, 2H), 3.40-3.28 (m, 4H), 2.25 (s, 3H), 2.10 (s, 3H), 1.97-1.91 (m, 4H). MS m/z: 402.3 (M+1).

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