Hydrochloric Acid → HCID 58815931, compound

Participants

Reaction Steps

To the compound of Example 117 (330 mg) in THF (5 mL) was added IN 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 organic solvent was removed under vacuum. The remaining water layer was diluted by water (4 mL). The water layer was extracted by n-butanol (10 mL×3). The combined n-butanol layer was washed by water (10 mL×2) and concentrated to give crude product (245 mg), which was purified by silica gel chromatography conducted on CombiFlash™ Sq 16×(gradient: 100% CH2Cl2 to 30% MeOH in CH2Cl2) to give 4-(4-{4-[(R)-((2S,5R)-4-allyl-2,5-dimethylpiperazin-1-yl)(3-hydroxy-phenyl)methyl]benzoyl}[1,4]diazepan-1-yl)butyric acid (180 mg; 57%). 1H NMR (300 MHz, DMSO-d6) δ 9.36 (bs, 1H), 8.31 (s, 1H), 7.40 (d, 2H, J=7.5 Hz), 7.30 (d, 2H, J=7.5 Hz), 7.12 (dd, 1H, J=8.0, 8.0 Hz), 6.66 (m, 3H), 5.78 (m, 1H), 5.20-4.97 (m, 3H), 3.59 (m, 2H), 3.47-3.34 (m, 2H), 3.18 (m, 1H), 2.86 (m, 1H), 2.73 (m, 2H), 2.60-2.49 (m, 7H), 2.42 (m, 1H), 2.21 (m, 2H), 2.10 (m, 1H), 1.83 (m, 2H), 1.69-1.55 (m, 3H), 1.06 (d, 3H, J=6.0 Hz), 0.94 (d, 3H, J=5.5 Hz).

Provenance & Evidence