Tetrahydrofuran → HCID 59287061, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl (2S)-cyclopentyl[({[(1R,2R)-2-pent-4-en-1-ylcyclopentyl]oxy}carbonyl)amino]acetate (1.97 g, 5.84 mmol) and LiOH.H2O (0.74 g, 17.51 mmol) in a 1:1 mixture of THF:H2O (60 mL) was heated to 40° C. The solution was stirred for 4 hours, then cooled to 20° C. The THF was removed under reduced pressure, and the residual aqueous solution was extracted with EtOAc. The organic phase was washed with H2O and brine, then dried over Na2SO4. Filtration and removal of the volatiles afforded the title compound (1.85 g, 98%) as an oil that was used directly in subsequent steps. 1H NMR (400 MHz, DMSO-d6) δ 12.25 (br s, 1H), 7.28 (d, J=8.1 Hz, 1H), 5.84-5.71 (m, 1H), 4.98 (d, J=17.4 Hz, 1H), 4.92 (d, J=10.1 Hz, 1H), 4.60-4.52 (m, 1H), 3.78 (t, J=8.0 Hz, 1H), 2.18-2.05 (m, 1H), 2.04-1.94 (m, 3H), 1.91-1.74 (m, 3H), 1.70-1.06 (m, 15H).

Provenance & Evidence