Lithium Hydroxide → (S)-2-Ethoxy-3-{2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]benzofuran-5-yl}propanoic acid

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Reaction Conditions

Reaction Steps

5-((S)-2-Ethoxy-3[(S)-4-benzyl-2-oxo-3-oxazolidinyl]-3-oxopropyl}-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]benzofuran (0.15 g, 0.26 mmol) was dissolved in tetrahydrofuran (5 ml). The solution was cooled to 0° C. and 0.5N lithium hydroxide (1.1 ml, 0.52 mmol) was added. After 15 minutes the bulk of the ethanol was removed, the residue was acidified with 1N HCl, diluted with water and extracted with ethyl acetate (3×). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The product was purified by flash chromatography (hexanes/ethyl acetate/acetic acid, 10:10:1) then recrystallized from hexanes/ethyl acetate and obtained as a white solid (48 mg, m.p. 129° C., [α]D =-12.5° (c 0.99, CDCl3)):

Provenance & Evidence