Methanol → HCID 56646832, compound

Participants

Reaction Steps

3-[(2R,5R)-5-Cyclohexyl-2-(2,3-dihydroxy-propyl)-2-methyl-3-oxo-morpholin-4-yl]-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester from the previous step was dissolved in 4.0 ml of THF and 0.3 mL of solution was taken out for the reaction. To the stirred solution was added THF (0.3 mL), MeOH (0.3 mL), water (0.3 mL), and LiOH.H2O (25.6 mg, 0.61 mmol, 10.0 equiv) and the resulting solution was stirred at room temperature for 30 minutes. The reaction was quenched by addition of 3.0 N HCl aqueous solution until pH=5. To the solution was then added EtOAc and the phases were separated. The aqueous layer was extracted by EtOAc. The organic layers were combined, dried (over Na2SO4) and concentrated. The residue was purified by HPLC (0.1% NH4OH, MeCN/H2O, 10%-90%) to give product (11 mg, 37.7% yield) as white solid. MS: 478 [M−H+].

Provenance & Evidence