Ethanol → 7-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane

HRID 515481노트

반응식

HRID 515481 반응식
[C:1]1([C@H:7]([N:9]2[CH2:15][CH2:14][CH:13]([C:16]3[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=3)[O:12][CH2:11][CH2:10]2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.Cl.[NH2:26]O.C(=O)(O)[O-].[Na+].[CH2:33]([OH:35])[CH3:34]>>[CH3:34][C:33]1[O:35][N:26]=[C:20]([C:19]2[CH:18]=[CH:17][C:16]([CH:13]3[O:12][CH2:11][CH2:10][N:9]([C@@H:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH3:8])[CH2:15][CH2:14]3)=[CH:23][CH:22]=2)[N:21]=1

참가 물질

6

반응물 5

HCID 702EthanolHCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 672813254-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzonitrile

생성물 1

HCID 672833297-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane

반응 조건

온도
80 °C

실험 절차

To a mixture of 4-[4-((R)-1-phenyl-ethyl)-[1,4]oxazepan-7-yl]-benzonitrile (diastereomer type A) (0.68 g, 2.2 mmol) in ethanol (5 mL) and water (3 mL) was added hydroxylamine hydrochloride (0.46 g, 6.6 mmol) and sodium bicarbonate (1.20 g, 11 mmol) at room temperature and the resulting mixture was heated to 80° C. After stirring for 2 hours, the reaction mixture was evaporated for removal of ethanol and diluted with water and chloroform. The organic phase was separated from aqueous phase and dried over anhydrous sodium sulfate. After concentration, half of the residue (0.39 g) was dissolved in xylene (3 mL) and dimethylacetamide dimethylacetal was added at room temperature. The mixture was refluxed for 3 hours and concentrated. The residual material was purified by flash column chromatography on silica gel to yield 7-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)-phenyl]-4-((R)-1-phenyl-ethyl)-[1,4]oxazepane (diastereomer type A) (0.33 g, 0.92 mmol, 83%).

후처리

  1. customthe reaction mixture was evaporated for removal of ethanol
  2. additiondiluted with water and chloroform
  3. customThe organic phase was separated from aqueous phase
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationAfter concentration, half of the residue (0.39 g)
  6. dissolutionwas dissolved in xylene (3 mL)
  7. additiondimethylacetamide dimethylacetal was added at room temperature
  8. temperatureThe mixture was refluxed for 3 hours
  9. concentrationconcentrated
  10. customThe residual material was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-9ded372dcac94746a0d0adacc19e6ae0
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108957B2

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