Methylamine → HCID 131727006, compound

HRID 2220361Notes

Reaction equation

HRID 2220361 reaction equation
[CH3:1][NH2:2].[Cl:3][C:4]1[CH:28]=[C:27]([Cl:29])C=C[C:5]=1O[C@@H](CCC)[C@@H](O)COS(C1C=CC(C)=CC=1)(=O)=O.[C:30]([C@@H:33]([C@H:35]([C:37]([O-:39])=[O:38])[OH:36])[OH:34])([O-:32])=[O:31].[O:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>>[C:30]([CH:33]([CH:35]([C:37]([OH:39])=[O:38])[OH:36])[OH:34])([OH:32])=[O:31].[Cl:29][C:27]1[CH:28]=[C:4]([Cl:3])[CH:5]=[CH:41][C:42]=1[O:43][CH:44]([NH:2][CH3:1])[CH:45]([OH:40])[CH2:30][CH2:33][CH2:35][CH3:37]

Participants

5

Reactant 4

HCID 6329MethylamineHCID 312751,4-DioxaneHCID 119400TartrateHCID 87730694HCID 87730694, compound

Product 1

HCID 131727006HCID 131727006, compoundYield 64%

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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
  7. customsonicating
  8. concentrationThe mixture is concentrated under reduced pressure
  9. dissolutionthe residue is dissolved in water
  10. temperaturefrozen at −78° C.
  11. customfreeze dried

Sources & evidence

ORD record
ord-357fdaf8f90343a29571de316d0ffe9a
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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