Methylamine → HCID 69197547, compound

Temperature

50 °C

Add methyl amine (5 mL, 40% wt in water) to a solution of (2S, 3S)-toluene-4-sulfonic acid 3-(3,5-dichloro-phenoxy)-2-hydroxy-hexyl ester (306 mg, 0.706 mmol) in 1,4-dioxane (10 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 HCl salt formation by dissolving in methanol (10 mL), adding solid ammonium chloride (32 mg, 0.598 mmol) and sonicating for 15 minutes. 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 (170 mg, 73%): δH (CD3OD, 400 MHz): 0.94 (dd, 3H, J=7, 7 Hz), 1.31-1.55 (m, 2H), 1.60-1.79 (m, 2H), 2.72 (s, 3H), 3.11 (dd, 1H, J=13, 10 Hz), 3.22 (dd, 1H, J=13, 3 Hz), 3.97-4.05 (m 1H), 4.37-4.45 (m, 1H), 7.00-7.04 (m, 3H). Exact Mass cacld. for C13H19O2NCl2 (M+ free base): 292.0871; found: 292.0879.

1. customseal the tube
2. temperatureThe mixture is cooled
3. concentrationconcentrated under reduced pressure
4. customPurification by medium pressure liquid chromatography
5. washeluting with 0-10% of 2N NH3/MeOH in dichloromethane
6. dissolutionby dissolving in methanol (10 mL)
7. customsonicating for 15 minutes
8. concentrationThe mixture is concentrated under reduced pressure
9. dissolutionthe residue is dissolved in water
10. temperaturefrozen at −78° C.
11. customfreeze dried

ORD record

ord-8b7f42107cf14087b2bc38aaff824098

Source dataset

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07417064B2