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Ammonia → tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

HRID 1350204
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인쇄 미리보기

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HRID 1350204 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24]OS(C3C=CC(C)=CC=3)(=O)=O)[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:36]>C1COCC1.CCOC(C)=O>[NH2:36][CH2:24][C:21]1[N:20]=[C:19]([C@H:10]([CH2:9][CH2:8][CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:23][N:22]=1
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참가 물질

5

반응물 2

HCID 222AmmoniaHCID 16747945tert-Butyl (3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)1,2,4-oxadiazol-5-yl]hexanoate

생성물 1

HCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate수율 94%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
40 °C

실험 절차

A soluton of tert-butyl(3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)-1,2,4-oxadiazol-5-yl]hexanoate (preparation 177) (1.2 g, 2.37 mmol) in THF (40 ml) was treated with concentrated ammonia solution and heated in a bomb at 40° C. for 18 hours. The reaction mixture was diluted with EtOAc and washed with sat. NaHCO3 solution followed by brine. The organic extract was dried over anhydrous MgSO4, filtered and the solvent removed under reduced pressure. The colourless oil was purified on a silica column eluting with a solvent gradient of pentane:EtOAc (4:1) gradually changing to (1:1) and then changing to DCM:MeOH:NH3 (95:5:0.5) to afford the title compound as a colourless oil (782 mg, 94%).

후처리

  1. washwashed with sat. NaHCO3 solution
  2. extractionThe organic extract
  3. dry with materialwas dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customThe colourless oil was purified on a silica column
  7. washeluting with a solvent gradient of pentane:EtOAc (4:1)

출처 및 근거

ORD 기록
ord-447e5dc0b6164fdc9bfc28568f0f7e09
출처 데이터셋
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07214694B2

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