Hydrochloric Acid → HCID 58815940, compound

Participants

Reaction Steps

To a solution of 1-{3-[(R)-[(2S,5R)-4-(3-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-hydroxy-phenyl)-methyl]-benzoyl}-piperidine-4-carboxylic acid ethyl ester (463 mg, Example 124) in THF (4 mL) was added 1N NaOH solution (3 mL). The reaction was stirred at room temperature overnight. The reaction solution was neutralized by the addition of 1 N HCl solution (3 mL). The resulting solution was concentrated under vacuum to give crude product, which was subjected to reverse phase C-18 column chromatography conducted on CombiFlash™ Sq 16×(gradient: 100% H2O to 100% MeOH) to give 1-{3-[(R)-[(2S,5R)-4-(3-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-(3-hydroxyphenyl)-methyl]-benzoyl}-piperidine-4-carboxylic acid (183 mg; 41%). 1H NMR (300 MHz, CD3OD) δ 7.48 (m, 2H), 7.37 (m, 2H), 7.27 (m, 1H), 7.16 (m, 3H), 7.04 (m, 1H), 6.71 (m, 3H), 5.21 (s, 1H), 4.47 (m, 1H), 4.13 (d, J=13.5 Hz, 1H), 3.66 (m, 1H), 3.51 (d, J=13.5 Hz, 1H), 3.09 (m, 2H), 2.81 (m, 3H), 2.68 (m, 1H), 2.55 (m, 1H), 2.30 (m, 1H), 2.06 (m, 2H), 1.83 (m, 1H), 1.65 (m, 2H), 1.21 (d, J=6.0 Hz, 3H), 1.15 (d, J=6.5 Hz, 3H).

Provenance & Evidence