Lithium Hydroxide → (2R)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-naphthalen-2-ylpropanoic acid

Participants

Reaction Steps

(2R)-2-(N-tert-Butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid methylester (15.0 g; 43.73 mmol) was dissolved in dioxane (150 ml) and cooled on an icebath. Water (115 ml) and lithium hydroxide (1.15 g; 48.10 mmol) were added. The reaction mixture was stirred 4 hours at room temperature. Ethyl acetate (300 ml) and water (200 ml) were added. Sodium hydrogensulfate (3%) was added until acidic reaction (pH=2.5). The organic phase was washed with water (200 ml) and dried (Magnesium sulfate). The solvent was removed in vacuo to afford 13.5 g of (2R)-2-(N-tert-Butoxycarbonyl-N-methylamino)-3-(2-naphthyl)propionic acid.

Provenance & Evidence