Ammonium Hydroxide → N6-Trityl-Lysinamide

Participants

Reaction Steps

A solution of compound 2 (1.49 g, 3.71 mmol) in 10 ml DMF was cooled to −78° C. in a pressure tube. Ammonia gas was bubbled though the solution until approximately 1 ml has added. Ammonium hydroxide solution (12 ml, 185.6 mmol, 50+ equivalents) was then added, and the tube allowed to warm to room temperature. The mixture was then sonicated for 20 minutes and heated to 55° C. while stirring. After 24 hours, the solution was golden in color, after which it was removed from the oil bath and cooled to −78° C. for 5 minutes before removing pressure cap. The solution was then allowed to warm to room temperature, and the solvent removed by reduced pressure distillation. The product was purified by flash column chromatography (Silica Gel, 8% methanol/92% CH2Cl2). and isolated as a clear golden oil (0.987 g. Yield: 68%). 1H NMR (CDCl3, 300 MHz) δ1.3-1.6 (m, 4H), 1.76 (m, 2H), 2.13 (t,2H), 3.33 (t, 1H) 7.14-7.52 (m, 15H) 13C NMR (CDCl3) 75 MHz) δ23.8, 30.9, 35.2, 43.6, 55.3, 71.0, 126.3, 127.9, 128.8, 146.4, 178.3; ESI-MS calculated for C25H29N3O 387.52; found 388.4 [M++1].

Provenance & Evidence