Methanol → HCID 86685805, compound

Participants

Reaction Steps

To a solution of (2S,4R)-methyl 1-((2S,3R)-2-(tert-butoxycarbonylamino)-3,7-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylate (4.3 g, 10 mmol) in THF/water (30 mL, 1:1) was added methanol (10 mL) followed by LiOH (1.3 g, 0.030 moles) 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 the desired product (2S,4R)-((2S,3R)-2-(tert-butoxycarbonylamino)-3,7-dimethylnon-8-enoyl)-4-hydroxypyrrolidine-2-carboxylic acid (3.2 g, 78% yield) as a white solid. 1H NMR (400 MHz, CDCl3): δ ppm 5.70-5.61 (m, 1H), 5.14-5.12 (d, J=8.8 Hz, 1H), 4.96-4.88 (m, 2H), 4.82-4.78 (t, J=8.4 Hz, 1H), 4.52 (bs, 1H), 4.27-4.23 (m, 1H), 3.57-3.53 (m, 3H), 2.48-2.42 (m, 1H), 2.33-2.28 (m, 1H), 1.88-1.82 (m, 2H), 1.45-1.42 (s, 9H), 1.29-1.21 (m, 3H), 0.98-0.93 (m, 7H) MS: MS m/z 411.2 (M++1).

Provenance & Evidence