Water → 2-{(2r)-2-(3,4-Dichlorophenyl)-4-[3,5-bis(trifluoromethyl)benzoyl]morpholin-2-yl}ethanol methanesulfonate

HRID 901980Notes

Reaction equation

HRID 901980 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@:9]2([CH2:31][CH2:32][OH:33])[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:30])[C:16]3[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=3)[CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>C(Cl)Cl>[CH3:41][S:42]([O:33][CH2:32][CH2:31][C@:9]1([C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[O:14][CH2:13][CH2:12][N:11]([C:15](=[O:30])[C:16]2[CH:17]=[C:18]([C:26]([F:28])([F:27])[F:29])[CH:19]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:21]=2)[CH2:10]1)(=[O:44])=[O:43]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 865997912-{(2R)-2-(3,4-dichlorophenyl)-4-[3,5-bis(trifluoromethyl)benzoyl]morpholin-2-yl}ethanol

Product 1

HCID 877403852-{(2r)-2-(3,4-Dichlorophenyl)-4-[3,5-bis(trifluoromethyl)benzoyl]morpholin-2-yl}ethanol methanesulfonateYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.68 g (11 mmol) of the obtained alcohol form was dissolved in methylene chloride (60 mL) and 2.3 mL (16.5 mmol) of triethylamine was added thereto under a nitrogen atmosphere. 1.02 ml (13.2 mmol) of methanesulfonyl chloride was added to the mixture under ice-cooling and the mixture was stirred at room temperature for 30 minutes under a nitrogen atmosphere. Water was added to the reaction mixture and the methylene chloride layer was washed with water and a saturated NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=3/2) to obtain 6.09 g (yield: 93%) of the title compound.

Workup

  1. temperaturecooling
  2. washthe methylene chloride layer was washed with water
  3. dry with materiala saturated NaCl solution and dried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluting solvent: hexane/ethyl acetate=3/2)

Sources & evidence

ORD record
ord-fc020781d3d845c185279a9ae5bdf6d4
Source dataset
uspto-grants-2008_04
Patent number
US07365067B2

Reaction notes

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