Methanol → HCID 86685804, compound

Participants

Reaction Steps

To a solution of (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,7-dimethylnon-8-enoate (2.7 g, 8.25 mmol) in THF/water (40 mL, 1:1) was added methanol (20 mL) followed by LiOH (0.987 g, 41.2 mmole) at room temperature. The reaction mass was stirred at room temperature overnight. Solvent was evaporated under reduced pressure and the residue was diluted with water (100 mL). The aqueous solution was acidified with aqueous 1.5 N HCl solutions to pH˜3 and extracted with ethyl acetate (100 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduce pressure to get crude compound. The crude compound was purified by column chromotography (Silica gel, 3% methanol in DCM) to get 2.1 g (85%) of desired compound as gummy liquid. 1H NMR (400 MHz, DMSO-D6): δ ppm 12.2-12.02 (bs, 1H), 6.92-6.85 (m, 1H) 5.72-5.66 (m, 1H), 4.98-4.85 (dd, J=1.6, 2.8 Hz, 2H), 4.03-3.95 (m, 1H), 2.58-2.56 (m, 1H) 2.15-2.02 (m, 1H), 1.45-1.36 (m, 10H), 1.27-1.21 (m, 5H), 0.95-0.93 (m, 3H), 0.84-0.74 (m, 3H).

Provenance & Evidence