2-Methylbutylamine → HCID 59620930, compound

Participants

Reaction Steps

To a mixture of Boc-Leu-OH (61.3 mg, 0.26 mmol), 2-methylbutylamine (0.046 ml, 0.40 mmol) and 3 ml of MeCN in a round bottom flask equipped with a magnetic stirring bar was added DIEA (0.092 ml, 0.53 mmol) followed by HBTU (120 mg, 0.32 mmol). The reaction mixture was stirred at room temperature for 16 hours at which point TLC analysis showed that the reaction was complete. The mixture was concentrated under reduced pressure. 10 ml of DCM was added and this mixture was washed with water (×3), citric acid (1M, ×3), and brine (×1), dried over Na2SO4 and concentrated under reduced pressure. The crude 1H NMR showed that the product was pure enough to carry over to the next step. 1H NMR (CDCl3, 300 MHz): δ 6.75 (b, 1H), 5.21 (b, 1H), 4.18 (b, 1H), 3.17 (m, 2H), 1.77-1.07 (m, 16H), 0.98 (m, 12H) ppm; 13C NMR (CDCl3, 75 MHz): δ 172.9, 156.0, 53.3, 45.1, 41.4, 35.0, 28.4, 27.1, 27.1, 27.0, 24.9, 23.0, 22.3, 17.2, 17.1, 11.4, 11.3 ppm. HRMS (ESI+) [M+H]+ calcd. for C16H33N2O3 301.2485, found 301.2489.

Provenance & Evidence