4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid methyl ester → 4-(2-((R)-2-((S,E)-3-hydroxyoct-1-enyl)-5-oxopyrrolidin-1-yl)ethylthio)butanoic acid

Participants

Reaction Steps

To a solution of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio] butanoic acid methyl ester (0.011 g, 0.03 mmol) in 2 mL of methanol at room temperature under an argon atmosphere was added an aqueous solution of sodium hydroxide (1 M, 4-5 drops). The reaction was stirred for 4 hours, evaporated under reduced pressure and treated with aqueous hydrochloric acid (1 M) until acidic. The residue was diluted with water (10 mL) and extracted with ethyl acetate. The organic solution was dried (brine, Na2SO4) and evaporated to yield 7.5 mg of 4-[(2-{(2R)-2-[(1E,3S)-3-hydroxyoct-1-enyl]-5-oxopyrrolidin-1-yl}ethyl)thio]butanoic acid: 1H NMR (300 MHz, CDCl3) δ partial spectrum 5.74 (dd, 1H, J=5.7, 15.6 Hz), 5.53 (dd, 1 H, J=8.2, 15.6 Hz), 4.11-4.20 (m with apparent q, 2 H, J=6.0 Hz), 3.62-3.81 (m with dd, 2 H, J=2.4, 10.2 Hz), 3.08-3.20 (m, 1 H); MS m/z (M+), 357.

Provenance & Evidence