Hydrochloric Acid → 4-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

Participants

Reaction Steps

66.6 mg (1.59 mmol) of lithium hydroxide monohydrate are added to a solution of 0.31 g (0.53 mmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(3-oxomorpholin-4-yl)propoxy]phenyl}-pent-4-en-1-yl]benzoate (Example 23A) in 2 ml of THF and 2 ml of water, and the mixture is stirred at room temperature for 18 h. The mixture is then adjusted to pH 2 using 1 M hydrochloric acid and extracted twice with ethyl acetate. The combined organic phases are dried over sodium sulfate. After filtration, the solvent is removed to dryness and the crude product is purified by preparative HPLC. This gives 89.5 mg (0.16 mmol, 30.3% of theory) of the title compound as a colorless solid.

Provenance & Evidence