4-Methylmorpholine → (R)-4-methyl-3-{4-[4-(4-methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-one

HRID 1804177Notes

Reaction equation

HRID 1804177 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.Cl.[CH3:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[O:26])=[CH:21][CH:20]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.CN1CCOCC1.[OH-].[Na+]>CO.C(Cl)(Cl)Cl>[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:30]2[CH2:31][CH2:32][CH:27]([C:25](=[O:26])[C:22]3[CH:21]=[CH:20][C:19]([CH3:18])=[CH:24][CH:23]=3)[CH2:28][CH2:29]2)=[O:14])=[CH:15][CH:16]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 27408174-(4-Methylbenzoyl)piperidine hydrochlorideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 58484719(R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid

Product 1

HCID 67381029(R)-4-methyl-3-{4-[4-(4-methylbenzoyl)piperidine-1-carbonyl]phenyl}oxazolidin-2-oneYield 85%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a mixture of (R)-4-(4-methyl-2-oxooxazolidin-3-yl)benzoic acid (633 mg) described in Preparation Example 37, (4-methylphenyl)piperidin-4-ylmethanone hydrochloride (719 mg) and 4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMT-MM) (1.2 g) were added chloroform (3 mL), methanol (3 mL) and N-methylmorpholine (330 μL), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 1N aqueous sodium hydroxide solution, 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) to give the title compound (989 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)

Sources & evidence

ORD record
ord-c0ae82b080cc43199afc6970cc813d07
Source dataset
uspto-grants-2013_01
Patent number
US08354401B2

Reaction notes

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