Diisopropylethylamine → HCID 58355735, 화합물

HRID 1260107노트

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HRID 1260107 반응식
[NH2:1][C@@H:2]1[CH2:7][C@H:6]([N:8]([C:13]([C:15]2[N:16]=[N:17][N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:19]=2[CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])=[O:14])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:3]1.C(N(C(C)C)CC)(C)C.Br[CH2:49][CH2:50][CH2:51][CH2:52][C:53](Cl)=[O:54]>C1COCC1.O>[CH3:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][C:19]1[N:18]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:17]=[N:16][C:15]=1[C:13]([N:8]([CH2:9][CH:10]([CH3:12])[CH3:11])[C@@H:6]1[CH2:5][N:4]([C:32]([O:34][C:35]([CH3:36])([CH3:38])[CH3:37])=[O:33])[CH2:3][C@H:2]([N:1]2[CH2:49][CH2:50][CH2:51][CH2:52][C:53]2=[O:54])[CH2:7]1)=[O:14]

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 5211735-Bromovaleryl chlorideHCID 58355545HCID 58355545, 화합물

생성물 1

HCID 58355735HCID 58355735, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

tert-Butyl (3R,5S)-3-amino-5-[{[5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazol-4-yl]carbonyl}(2-methylpropyl)amino]piperidine-1-carboxylate (150 mg) was dissolved in THF (3 ml), diisopropylethylamine (74 μl) and 5-bromovaleryl chloride (42 μl) were added at 0° C. and the mixture was stirred at 0° C. for 1 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in THF (10 ml), potassium tert-butoxide (96 mg) was added at 0° C. and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel chromatography, and a fraction eluted with ethyl acetate-hexane (1:3-1:0) was concentrated under reduced pressure to give the object product (150 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe residue was dissolved in THF (10 ml)
  6. additionpotassium tert-butoxide (96 mg) was added at 0° C.
  7. stirringthe mixture was stirred at room temperature for 1 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. additionthe residue was diluted with water
  10. extractionthe mixture was extracted with ethyl acetate
  11. washThe extract was washed with saturated brine
  12. dry with materialdried over anhydrous sodium sulfate
  13. concentrationconcentrated under reduced pressure
  14. washa fraction eluted with ethyl acetate-hexane (1:3-1:0)
  15. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-194cd61092b6417ab61c5c073b3568d3
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466282B2

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