Citric Acid → N-((1,1-Dimethylethoxy)carbonyl)-L-alanyl-L-alanine

Participants

Reaction Steps

To a solution of LiOH.H2O (275 mg, 6.56 mmol) in a mixture of solvents MeOH: H2O (10.9 mL: 3.6 mL) was added Boc-Ala-Ala-OMe (1.2 g, 4.38 mmol) and stirred for 4 hours at r.t. The solution was acidified to pH 2 with saturated aqueous solution of citric acid and the mixture was extracted with EtOAc (3×20 mL). The organic layer was dried over Na2SO4 and concentrated under vacuum to give the desired product Boc-Ala-Ala-OH as a highly viscous and hygroscopic oil in quantitative yields (1.14 g). The product was taken for further reactions directly without any purification.

Provenance & Evidence