Imidazole → HCID 178455368, 화합물

HRID 25561노트

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HRID 25561 반응식
[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([OH:17])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:8][C:9](=[O:18])[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][Si:28]([C:25]([CH3:27])([CH3:26])[CH3:24])([CH3:30])[CH3:29])[CH2:13][CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 178523817HCID 178523817, 화합물

생성물 1

HCID 178455368HCID 178455368, 화합물수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
50 °C

실험 절차

To 10 g (40.1 mmol) trans-4-Hydroxy-cyclohexylcarbamic acid benzyl ester in 40 ml DMF, 4.09 g (60.1 mmol, 1.5 eq) imidazole and 6.65 g (44.1 mmol, 1.1 eq) TBDMSCl in 20 ml DMF were added at 0° C. The mixture was warmed to 50° C. and stirred at that temperature for 2 h. A saturated solution of NaHCO3 was added, the mixture was concentrated and redissolved in ether/water. The phases were separated and the inorganic phase was extracted with ether. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated. The crude product was purified on silica gel with hexane:EtOAc 5:1 as eluent yielding 11.8 g (81%) trans-[4-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester as colorless gum, MS: 348 (M−CH3).

후처리

  1. concentrationthe mixture was concentrated
  2. dissolutionredissolved in ether/water
  3. customThe phases were separated
  4. extractionthe inorganic phase was extracted with ether
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe crude product was purified on silica gel with hexane:EtOAc 5:1 as eluent

출처 및 근거

ORD 기록
ord-0d568f7c46584bf6a125c9dd69622b4c
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858651B2

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