Trifluoroacetic acid → Glycine iodopropargyl ester trifluoroacetate

Participants

Reaction Conditions

Reaction Steps

N-t-Butoxycarbonyl glycine iodopropargyl ester (Compound #1) (4.20 g., 12.39 mmole) was dissolved in anhydrous dichloromethane (20 ml.), cooled to 0° C. with an ice-bath, and treated with 10 ml. of trifluoroacetic acid. The reaction mixture was stirred magnetically at 0° C. for 1 hour and then allowed to warm to ambient temperature. The volatile solvents were removed under reduced pressure leaving a clear syrup which crystallized on standing to a white solid (4.20 g., 96% yield) as the desired trifluoroacetate salt product. m.p. 130°-131° C. 1H-NMR (200 MHz, DMSOd6) δ=3.92, s, 2H; 5.00, s; 2H; s; 9.1, broad m. IR (KBr) 1605, 1670, 1765, 2205, 2640 cm-1.

Provenance & Evidence