Lithium Hydroxide → HCID 22949340, compound

Participants

Reaction Steps

4-((1R)-1-{[(1R)-1-(3-Ethoxycarbonyl-[1,2,4]oxadiazol-5-yl)-2-(2-naphthyl)ethyl]-N-methylcarbamoyl}-2-(2-naphthyl)-ethylcarbamoyl)piperidine-1-carboxylic acid tert-butyl ester(0.79 g, 1.06 mmol) was dissolved in dioxane (5.5 ml). Water (3 ml) and solid lithium hydroxide (0.03 g) was added. After 18 h at 20° C. the reaction mixture was diluted with water (15 ml) and extracted with tert-butyl-methylether (2×10 ml). The aqueous phase was acidified with 1N aqueous sodium hydrogenphosphate (2.5 ml) and extracted with tert-butyl-methylether (3×40 ml). The collected organic phases were dried (magnesium sulfate) and concentrated in vacuo. The residue was chromatographed on silica (60 g) using a mixture of dichioromethane and 10% ammonia in ethanol (4:1) as eluent to give 0.41 g of 4-(1-{[1-(3-carboxy-[1,2,4]oxadiazol-5-yl)-2-(2-naphthyl)ethyl]-N-methylcarbamoyl}-2-(2-naphthyl)-ethylcarbamoyl)piperidine-1-carboxylic acid tert-butylester.

Provenance & Evidence