L-Malic Acid → HCID 131729737, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL round flask was charged with Sitagliptin free base (5 g, 12 mmol) and a mixture of ethyl acetate:ethanol (5:0.8 v/v, 25 mL) was added. The mixture was mechanically stirred and heated to 60° C. until complete dissolution. The solution was then cooled to room temperature. In parallel, L-malic acid (1.65 g, 12 mmol) was completely dissolved in a mixture of ethyl acetate:ethanol (5:0.8 v/v, 10 mL) at 60° C. and then cooled to room temperature. The solution of the L-malic acid was then added dropwise to the solution of Sitagliptin free base over a period of 10 minutes while stirring at room temperature with the rotation speed of 310 rpm. The obtained white gel-paste reaction mixture was stirred at room temperature for about 69 hours. The obtained massive white precipitate was isolated by vacuum filtration, washed with cold mixture of ethyl acetate:ethanol (5:0.8 v/v, 2×10 mL) and dried in a vacuum oven at 40° C. for 23 hours to give Sitagliptin L-malate (5.99 g, 92% w/w yield).

Provenance & Evidence