1,4-Dioxane → HCID 10482868, compound

Participants

Reaction Steps

To a stirred solution of methyl N-[α-methyl-N-[(tricyclo[3.3.1.13,7 ]dec-2-yloxycarbonyl)-DL-tryptophyl]-N-(2-phenylethyl)glycinate (285 mg, 0.5 mmol) in dioxane (10 mL) and water (5 mL) was added lithium hydroxide-1-hydrate (42 mg, 1.0 mmol) and the resulting mixture was stirred overnight at room temperature. The reaction mixture was concentrated, acidified with dilute HCl, and extracted with ethyl acetate (2×50 mL). After drying over magnesium sulfate and concentration, flash column chromatography yielded the title compound which was crystallized from ethyl acetate and hexane to give 80 mg (29%) of white solid, mp 100°-105° C. IR (KBr) 3388 2908, 2855 1710 cm-1 ; NMR (250 MHz DMSO, 70° C.) 1.30 (3H, s), 1.1-1.58 (2H, m), 1.58-2.18 (12H, m), 2.56-2.92 (2H, m), 2.92-3.6 (4H, m), 3.6-4.26 (4H, m), 4.76 (1H, br s), 6.82-7.38 (9H, m), 7.45 (1H, d, J 7.7 Hz), 10.70 (1H, br s).

Provenance & Evidence