Hydrochloric Acid → HCID 89930806, compound

Participants

Reaction Steps

To a solution of methyl 4-((((3S,5S)-1-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-5-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)pyrrolidin-3-yl)oxy)methyl)benzoate (1.35 g, 1.91 mmol) in THF (5 mL) and MeOH (3 mL) was added a solution of NaOH (0.31 g, 7.64 mmol) in water (6 mL). The reaction mixture was stirred at rt for 4 h, acidified with 1N HCl and extracted with ethyl acetate. The organic layer was separated, washed with brine, and dried over MgSO4. The filtrate was concentrated in vacuo to give the title compound as a white solid (1.30 g, 98%). 1H NMR (DMSO-d6) δ 8.01 (d, J=8.6 Hz, 0.5H), 7.91 (d, J=8.4 Hz, 1.5H), 7.43 (d, J=8.4 Hz, 2H), 7.24 (d, J=7.7 Hz, 1H), 7.15-6.98 (m, 3H), 4.98-4.83 (m, 1H), 4.60 (s, 2H), 4.47 (d, J=9.0 Hz, 1H), 4.34 (t, J=7.7 Hz, 1H), 4.21 (t, J=6.2 Hz, 1H), 4.12-4.05 (m, 1H), 3.86-3.71 (m, 1H), 3.54 (dd, J=10.2, 6.1 Hz, 1H), 2.81-2.65 (m, 5H), 2.45-2.36 (m, 1H), 2.02-1.92 (m, 1H), 1.86-1.56 (m, 4H), 1.40 (br. s., 9H), 1.26-1.15 (m, 3H), 1.03-0.86 (m, 9H); MS(ESI+) m/z 693.6 (M+H)+.

Provenance & Evidence