Lithium hydroxide, monohydrate → (R)-2-((S)-1-Hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid

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Reaction Steps

A solution of (R)-2-((S)-1-hydroxy-2-morpholin-4-yl-2-oxo-ethyl)-5-phenyl-pentanoic acid methyl ester (230 mg, 0.69 mmol) and LiOH.H2O (57.5 mg, 1.37 mmol) in a mixture of THF and water (2:1, 6 ml) was stirred at room temperature for 2.5 hrs. The reaction was diluted with water and THF removed under reduced pressure. The pH of the aqueous solution was adjusted to pH5 with 1N HCl and extracted with ethyl acetate. The combined organic extracts were dried over MgSO4 and evaporated under reduced pressure to give the title compound as white solid (180 mg); 1H NMR (CDCl3) δ 1.92–1.60 (m, 4H), 2.75–2.60 (m, 3H), 3.78–3.45 (m, 9H), 4.5 (d, J=8 Hz, 1H), 7.35–7.18 (m, 5H); MS: 322(MH+).

Provenance & Evidence