Diisopropylethylamine → (S)-2-Amino-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-3-methyl-butyramide

Participants

Reaction Steps

Tert-butyloxycarbonyl-L-valine (21.7 mg), N,N-diisopropyl-ethylamine (35 uL), N-[(dimethylamino)-1H-1,2,3-triazolo-[4,5-b]pyridin-1-yl-methylene]-N-methyl-methanaminium hexafluoro-phosphate N-oxide (0.38 g) and 2,6,N′-trimethyl-N′-(4-trifluoromethyl-benzyl)-benzene-1,4-diamine (15.4 mg) were mixed in dry N,N-dimethylformamide (0.2 mL) and stirred under argon for 2 hours. Brine (2 mL) was added and the reaction mixture was extracted with ethyl acetate (2×2 mL). The combined organic phases were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. 15.4 mg (61% yield) of the N-Boc-protected title compound was isolated and it was dissolved in trifluoroacetic acid/dichloromethane (1:1, 2 mL) and stirred at 25° C. for 30 minutes. The reaction mixture was concentrated in vacuo to furnish 18 mg (96% yield) of the title compound. LC-MS-TOF (m/z) 408 (MH+); tR=2.19, (UV, ELSD) 93%, 98%.

Provenance & Evidence