Diisopropylethylamine → (R)-3-(3-(2-chloro-4-(trifluoromethyl)phenyl)ureido)-4-(trimethylammonio)-butanoate

Participants

Reaction Steps

To a solution of (R)-aminocarnitine (35 mg, 0.22 mmol) and diisopropylethylamine (0.11 mL, 0.65 mmol) in MeOH (2 mL) was added 2-chloro-1-isocyanato-4-(trifluoromethyl)benzene (67 uL, 0.44 mmol) and the reaction stirred at room temperature overnight. The MeOH was removed in vacuo and the residue titurated several times with 1:1 ether/EtOAc, the resulting solid was filtered and dried to give the title compound as a white powder (15 mg, 18%). NMR (300 MHz, CD3OD) δ 8.37 (m, 1H), 7.68 (m, 1H), 7.53 (m, 1H), 4.29 (m, 1H), 3.78-3.48 (m, 2H), 3.25 (s, 9H), 2.70-2.49 (m, 2H); MS ESI 382.1 [M+H]+, calcd for [C15H19ClF3N3O3+H]+ 382.78.

Provenance & Evidence