Lithium hydroxide, monohydrate → HCID 59038469, compound

Participants

Reaction Steps

To a solution of (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid methyl ester (Example 82; 3.00 g, ˜8.5 mmol) in tetrahydrofuran/methanol/water (3:1:1; 20 mL) was added lithium hydroxide monohydrate (1.43 g, 34 mmol). The mixture was allowed to stir at room temperature for 4 h and then concentrated in vacuo to remove tetrahydrofuran and methanol. The concentrate was diluted with water and extracted with three portions of ethyl acetate. The organic extracts were discarded and the aqueous layer was acidified with 1N hydrochloric acid solution. Ethyl acetate was added and the resulting colorless solid was recovered by filtration and washed with ethyl acetate. The layers in the filtrate were separated and the organic phase was dried (MgSO4), filtered and concentrated. The resulting residue was combined with the previously recovered solid to give (R)-2-chloro-4-[[1-(naphthalen-1-yl)ethylamino]carbonyl]benzoic acid (2.42 g, 84% yield).

Provenance & Evidence