Lithium Hydroxide → HCID 57988338, compound

Participants

Reaction Steps

To a solution of (2S,4R)-methyl 4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(propylsulfonyl)pyrrolidine-2-carboxylate (1.52 g, 2.372 mmol) in THF (20.00 mL) and MeOH (20 mL) was added pre-made solution of lithium hydroxide (0.199 g, 4.74 mmol) in water (20.00 mL). The formed cloudy solution was stirred at rt for 3 h. Removed the volatiles in vacuo. The residue was acidified with 1M HCl to pH 3, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated in vacuo to afford the desired product (2S,4R)-4-(biphenyl-4-yl)-1-((S)-2-(tert-butoxycarbonylamino)non-8-enoyl)-4-(propylsulfonyl)pyrrolidine-2-carboxylic acid (1.45 g, 2.198 mmol, 93% yield) as a white foam. 1H NMR (400 MHz, MeOD) δ ppm 0.97 (t, J=7.53 Hz, 3 H) 1.36-1.55 (m, 12 H) 1.55-1.82 (m, 4 H) 2.10 (q, J=6.61 Hz, 2 H) 2.81 (dd, J=8.66, 6.65 Hz, 2 H) 2.91 (dd, J=12.92, 10.42 Hz, 1 H) 3.28 (d, J=7.28 Hz, 1 H) 4.20 (dd, J=9.91, 7.40 Hz, 1 H) 4.37 (d, J=11.04 Hz, 1 H) 4.52 (t, J=6.90 Hz, 1 H) 4.95 (dd, J=10.16, 1.13 Hz, 2 H) 4.98-5.07 (m, 1 H) 5.13 (d, J=11.04 Hz, 1 H) 5.77-5.94 (m, 1 H) 7.33-7.42 (m, 1 H) 7.48 (t, J=7.53 Hz, 2 H) 7.65 (d, J=7.53 Hz, 2 H) 7.72-7.78 (m, 2 H) 7.93 (d, J=8.28 Hz, 2 H). LC-MS (retention time: 1.99 min, method A), MS m/z 627 (M+H).

Provenance & Evidence