Methylamine → HCID 131727006, compound

Participants

Reaction Conditions

Reaction Steps

Add methyl amine (3 mL, 40% wt in water) to a solution of (2S,3S)-toluene-4-sulfonic acid 3-(2,4-dichloro-phenoxy)-2-hydroxy-hexyl ester (266 mg, 0.614 mmol) in 1,4-dioxane (6 mL) in a heavy walled screw top sealed tube, seal the tube, and heat at 50° C. overnight. The mixture is cooled and concentrated under reduced pressure. Purification by medium pressure liquid chromatography eluting with 0-10% of 2N NH3/MeOH in dichloromethane is followed by L-tartrate salt formation by dissolving in methanol, adding L-tartrate (65.6 mg, 0.437 mmol) and sonicating. The mixture is concentrated under reduced pressure and the residue is dissolved in water, frozen at −78° C., and freeze dried to afford the title compound as a colorless solid (172.8 mg, 64%): δH (CD3OD, 400 MHz): 0.94 (dd, 3H, J=8, 8 Hz), 1.34-1.55 (m, 2H), 1.64-1.82 (m, 2H), 2.73 (s, 3H), 3.17 (dd, 1H, J=12, 10 Hz), 3.33 (dd, 1H, J=12, 3 Hz), 4.06-4.13 (m 1H), 4.40-4.48 (m, 3H),7.17 17(d, 1H, J=9Hz),7.25 17(dd, 1H, J=9, 3Hz),7.40 17 (d, 1H, J=3Hz).

Provenance & Evidence