Water → tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

HRID 1260114노트

반응식

HRID 1260114 반응식
Cl[C:2](Cl)(Cl)[C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.[N:14]1([C:20]([C@@H:22]2[CH2:27][C@H:26]([NH:28][CH2:29][CH2:30][CH3:31])[CH2:25][N:24]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:23]2)=[O:21])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.[OH2:39]>C1COCC1.C(=O)(O)[O-].[Na+]>[NH:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[C:2]([N:28]([CH2:29][CH2:30][CH3:31])[C@H:26]1[CH2:27][C@@H:22]([C:20]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:21])[CH2:23][N:24]([C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH2:25]1)=[O:39]

참가 물질

6

반응물 3

HCID 962WaterHCID 77133Benzimidazole, 2-trichloromethyl-HCID 58355640tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate

생성물 1

HCID 58355218tert-butyl (3S,5R)-3-[(1H-benzimidazol-2-ylcarbonyl)(propyl)amino]-5-(morpholin-4-ylcarbonyl)piperidine-1-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매2회

실험 절차

2-(Trichloromethyl)-1H-benzimidazole (1.09 g) and tert-butyl (3R,5S)-3-(morpholin-4-ylcarbonyl)-5-(propylamino)piperidine-1-carboxylate (1.49 g) were dissolved in THF (120 ml), sodium hydrogen carbonate (3.52 g) and water (60 ml) were added and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with aqueous sodium bicarbonate, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to basic silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (2:8-10:0) was concentrated under reduced pressure to give the object product (1.97 g).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washa fraction eluted with ethyl acetate-hexane (2:8-10:0)
  6. concentrationwas concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-1af8277b28f8452eae9a921793f3e997
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08466282B2

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