Lithium hydroxide, monohydrate → HCID 56646613, compound

Participants

Reaction Steps

To a solution of 3-[(2R,5R)-5-cyclohexyl-2-((R)-2-hydroxy-propyl)-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (650 mg, 1.41 mmol, 1.0 equiv) in THF (10 mL), MeOH (5 mL) and water (5 mL) was added LiOH.H2O (177 mg, 4.22 mmol, 3.0 equiv). The resulting solution was stirred at room temperature for 2 hours. The volatile solvent was removed under vacuum and to the residue was added water (15 mL). The mixture was cooled to 0° C. and acidified by addition of 3.0 N HCl aqueous solution until pH=1. The precipitate was isolated by filtration to give product (586 mg, 93%) as white solid. MS: 448.3 [M−H+]. 1H NMR (400 MHz, CD3OD): 1.09-1.31 (m, 8H) 1.32 (s, 9H) 1.45-1.85 (m, 5H) 1.89-2.10 (m, 3H) 3.56-3.61 (m, 1H) 3.93-4.00 (m, 1H) 4.00-4.10 (m, 1H) 4.12-4.22 (m, 2H) 6.99 (s, 1H).

Provenance & Evidence