Chloroform → (R)-4-methyl-3-{4-[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one hydrochloride

HRID 1804209Notes

Reaction equation

HRID 1804209 reaction equation
[CH3:1][C@@H:2]1[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=1.[CH3:17][C:18]1[C:19]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.C(Cl)(Cl)[Cl:54]>O.CO>[ClH:54].[CH3:1][C@@H:2]1[CH2:6][O:5][C:4](=[O:7])[N:3]1[C:8]1[CH:9]=[CH:10][C:11]([C:12]([N:31]2[CH2:32][CH2:33][N:28]([C:19]3[C:18]([CH3:17])=[CH:23][C:22]([C:24]([F:27])([F:25])[F:26])=[CH:21][N:20]=3)[CH2:29][CH2:30]2)=[O:14])=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acidHCID 584847291-(3-Methyl-5-trifluoromethylpyridin-2-yl)piperazine

Product 1

HCID 67380787(R)-4-methyl-3-{4-[4-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine-1-carbonyl]phenyl}oxazolidin-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of (R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (664 mg) described in Preparation Example 37, 1-(3-methyl-5-trifluoromethylpyridin-2-yl)piperazine (736 mg) described in Preparation Example 51 and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.2 g) were added chloroform (5 mL) and methanol (5 mL), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and the solvent was evaporated. The residue was purified by column chromatography (hexane:ethyl acetate). The obtained compound was dissolved in ethyl acetate (20 mL), 4N hydrogen chloride/ethyl acetate (1 mL) was added, and the mixture was filtered to give the title compound (310 mg).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. washThe organic layer was washed with saturated brine
  3. customthe solvent was evaporated
  4. customThe residue was purified by column chromatography (hexane:ethyl acetate)
  5. dissolutionThe obtained compound was dissolved in ethyl acetate (20 mL)
  6. addition4N hydrogen chloride/ethyl acetate (1 mL) was added
  7. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-f4982234eebb423d8545c7716a34186f
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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