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

HRID 1804177노트

반응식

HRID 1804177 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-c0ae82b080cc43199afc6970cc813d07
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354401B2

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