Tetrahydrofuran → HCID 59287061, compound

HRID 1255510Notes

Reaction equation

[CH:1]1([C@H:6]([NH:11][C:12]([O:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])=[O:13])[C:7]([O:9]C)=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O.C1COCC1>O>[CH:1]1([C@H:6]([NH:11][C:12]([O:14][C@@H:15]2[CH2:19][CH2:18][CH2:17][C@H:16]2[CH2:20][CH2:21][CH2:22][CH:23]=[CH2:24])=[O:13])[C:7]([OH:9])=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 20 °C

Procedure

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).

Workup

customThe THF was removed under reduced pressure
extractionthe residual aqueous solution was extracted with EtOAc
washThe organic phase was washed with H2O and brine
dry with materialdried over Na2SO4
filtrationFiltration and removal of the volatiles

Sources & evidence

ORD record: ord-a67c1ac108dd4659b36589693fd39a92
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461107B2

Reaction notes

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