Dimethyl Sulfoxide → methyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-3,5-difluorobenzoate

HRID 1691764노트

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HRID 1691764 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:13])[C:11]=1F)[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[C:24]1([C@H:34]([N:36]([CH2:44][CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH:46]2[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)[C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH3:35])[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1>C1COCC1.O>[C:39]([O:38][C:37]([N:36]([CH2:44][CH:45]1[CH2:50][CH2:49][N:48]([C:11]2[C:10]([F:13])=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[F:1])[CH2:47][CH:46]1[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)[C@@H:34]([C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=1)[CH3:35])=[O:43])([CH3:40])([CH3:41])[CH3:42]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 11430Potassium CarbonateHCID 2783211Methyl 3,4,5-trifluorobenzoateHCID 59178521HCID 59178521, 화합물

생성물 1

HCID 66906144methyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-3,5-difluorobenzoate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

To a mixture of 116 mg of methyl 3,4,5-trifluorobenzoate, 113 mg of potassium carbonate, and 2.0 mL of DMSO was added 181 mg of a solution of tert-butyl [(1R)-1-(1-naphthyl)ethyl][(3-phenylpiperidin-4-yl)methyl]carbamate in 3.0 mL of THF at room temperature. It was stirred at 100° C. overnight, and then cooled. To the reaction mixture was added water, followed by extraction with ethyl acetate, and the organic layer was then washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure to obtain 248 mg of methyl 4-[4-({(tert-butoxycarbonyl)[(1R)-1-(1-naphthyl)ethyl]amino}methyl)-3-phenylpiperidin-1-yl]-3,5-difluorobenzoate as a crude product. FAB+: 615

후처리

  1. temperaturecooled
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was then washed with water and saturated brine in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-8a3d8ab748ce43f29d56440161c5f8a0
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153658B2

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