Diisopropylethylamine → HCID 25065923, compound

Participants

Reaction Steps

To a solution of (R)-aminocarnitine (17 mg, 0.11 mmol) and diisopropylethylamine (55 uL, 0.32 mmol) in MeOH (2 mL) was added 2-(4-isocyanatophenyl)thiophene (43 mg, 0.22 mmol) and the reaction stirred for 18 h. The MeOH was removed in vacuo and the residue stirred with 1:1 ether/EtOAc. Impurities dissolved into the ether/EtOAc which were discarded and the remaining material taken up into 90:10 CH2Cl2/MeOH and then loaded onto a short SiOH plug. The title compound was eluted by increasing MeOH content in 10% steps to 60%. The compound was then taken up into 90:10 CH2Cl2/MeOH and filtered through a plug of celite which gave after drying the title compound as a white powder (5 mg, 13%). 1H NMR (400 MHz, CD3OD) δ 7.53 (d, 2H, J=8.0 Hz), 7.42 (d, 2H, J=8.0 Hz), 7.29 (s, 2H), 7.05 (s, 1H), 4.65-4.63 (m, 1H), 3.77-3.53 (m, 2H), 3.23 (s, 9H), 2.58-2.48 (m, 2H); MS ESI 362.1 [M+H]+, calcd for [C18H23N3O3S+H]+ 362.46.

Provenance & Evidence