Diisopropylethylamine → HCID 67606716, compound

Participants

Reaction Steps

A solution of Boc-N(Me)Ala-OH (181 mg, 0.89 mmol) in NMP (6 mL) was cooled to 0° C. and treated with HATU (345 mg, 0.91 mmol) and DIPEA (0.20 mL, 1.2 mmol). After 10 min, amine 82 (400 mg, 0.80 mmol) in NMP (5 mL) was added and the reaction mixture was allowed to warm to ambient temperature. After 16 h, the solution was diluted with EtOAc, washed successively with 1M HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous Na2SO4, filtered and concentrated to give 83 (546 mg) as an off-white foam that was used without further purification. 1H NMR (CDCl3, 300 MHz): δ7.37-7.29 (m, 5H), 7.01 (app q, J=9.3 Hz, 1H), 6.66 (m, 1H), 6.53 (m, 1H), 5.19-5.09 (m, 2H), 4.69 (m, 1H), 4.62 (d, J=9.0 Hz, 1H), 4.49-4.44 (m, 2H), 4.05-3.97 (m, 1H), 3.84-3.77 (m, 1H), 3.48-3.36 (m, 1H), 2.79 (s, 3H), 1.50 (s, 9H), 1.32 (d, J=6.9 Hz, 3H), 0.98 (s, 9H) ppm. Mass spectrum, m/z [687.9] (M+H)+.

Provenance & Evidence