Sodium Hydroxide → HCID 9907375, compound

Participants

Reaction Steps

A methanol (10 mL) solution of 4-{2-[(R)-2-((S)-(E)-5-Cyclopropyl-3-hydroxy-pent-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric acid methyl ester from step (4, 98 mg, 0.25 mmol) was treated with sodium hydroxide (0.3 mL, 5 M aqueous) and stirred at ambient temperature for 3 hours. The volatiles were removed under a stream of nitrogen and the mixture was partitioned between water and ethyl ether. The aqueous layer was rendered acidic with hydrochloric acid (12 M aqueous) and extracted with ethyl acetate (3×15 mL). The combined organic extracts was stored over anhydrous sodium sulfate. 4-{2-[(R)-2-((S)-(E)-5-Cyclopropyl-3-hydroxy-pent-1-enyl)-6-oxo-piperidin-1-yl]-ethylsulfanyl}-butyric acid (94 mg, 0.25 mmol) was obtained following filtration and removal of the volatiles as an oil: 1H NMR (300 MHz, CDCl3) δ 6.7 (br.s, 1 H), 5.58-5.63 (m, 2 H), 4.18-4.22 (m, 1 H), 4.02-4.07 (m, 1 H), 3.87-3.98 (m, 1 H), 2.98-3.08 (m, 1 H), 2.62-2.72 (m, 2 H), 2.59 (t, J=6.9 Hz, 2 H), 2.36-2.49 (m, 4 H), 1.61-1.99 (m, 8 H), 1.22-1.30 (m, 2 H), 0.59-0.71 (m, 1 H), 0.40-0.46 (m, 2 H), 0.00-0.06 (m, 2 H); MS: m/z M+1, 370.

Provenance & Evidence