Hydrochloric Acid → HCID 53246498, compound

Participants

Reaction Steps

To the crude mixture of ethyl 2-(3-acetyl-2,5-dimethyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetate (25 mg, 0.055 mmol) in MeOH:THF:water 3:3:1 (5 ml total) was added LiOH (3.96 mg, 0.165 mmol) and the resulting mixture was stirred for 30 min. To this mixture were added EtOAc (3 mL) and HCl (1N aq., 3 mL). The ethyl acetate layer was separated and dried over Na2SO4, filtered and subjected to column chromatography on silica gel (0 to 100% ethyl acetate in hexanes, followed by 0 to 20% MeOH in ethyl acetate). Collection and concentration of pertinent fractions resulted in the isolation of 2-(3-acetyl-2,5-dimethyl-4-(2-(phenylsulfonyl)benzyl)-1H-pyrrol-1-yl)acetic acid (10.5 mg, 45%) as a tan solid. 1H NMR (CDCl3/400 MHz) 8.23-8.20 (m, 1H), 7.84 (d, 2H), 7.51 (t, (t, 1H), 7.48-7.40 (m, 2H), 7.36-7.30 (m, 2H), 6.84-6.21 (m, 1H), 4.51 (s, 2H), 4.09 (s, 2H), 2.37 (s, 3H), 1.79 (s, 3H), 1.62 (s, 3H). MS m/z=426.4 (M+1).

Provenance & Evidence