HCID 17757682, compound → HCID 57935133, compound

Participants

Reaction Steps

A solution of (2S,3S)—N-(2-chloro-4-iodo-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (prepared as described in example 110) (50 mg, 0.079 mmol) was dissolved in methanol (3 mL) and stirred at ambient temperature for 4 days. The resulting mixture of isomers was concentrated in vacuo and then purified by super-critical fluid chromatography using a Chiracel OJ column eluted with carbon dioxide at 100 bar and 30° C. modified with 35% v/v ethanol in acetonitrile eluted at 2 mL/minute. The first eluted compound was collected and concentrated in vacuo to obtain (2S,3S)—N-(2-chloro-4-iodo-phenyl)-2-{(S)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (14.6 mg, 29%) The compound eluted second was identical with (2S,3S)—N-(2-chloro-4-iodo-phenyl)-2-{(R)-4-[4-(2-hydroxy-ethoxy)-phenyl]-2,5-dioxo-imidazolidin-1-yl}-3-phenyl-butyramide (18.1 mg, 36%). LC-MS (reverse phase HPLC, C18 column, water/acetonitrile gradient): Rt=2.40 minutes, Obs. Mass (M+Na+), 656. Calcd. Mass, 640 for C27H25CIIN3NaO5+. 1H NMR (DMSO-d6, 300 MHz) OH 9.98 (s, 1H), 8.61 (s, 1H), 4.81 (d, J=11.8 Hz, 1H) ppm (characteristic resonances).

Provenance & Evidence