Water → 4-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester

HRID 2055131노트

반응식

HRID 2055131 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH3:15])=[O:13])(OCC)=O)C.[CH3:16][C:17]([N:21]1[CH:25]=[C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[N:23]=[CH:22]1)([CH3:20])[CH:18]=O.O>C1COCC1>[CH3:15][O:14][C:12](=[O:13])[CH2:11][CH2:18][C:17]([CH3:20])([N:21]1[CH:25]=[C:24]([C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[N:23]=[CH:22]1)[CH3:16]

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 66113Methyl diethylphosphonoacetateHCID 235114292-Methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde

생성물 1

HCID 207376634-Methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester수율 75%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of sodium hydride (1.2 eq) in THF was added slowly methyl diethylphosphonoacetate (1.2 eq) at 0° C. under dry conditions and the mixture was stirred at room temperature for 30 minutes. A solution of 2-methyl-2-(4-pyridin-3-yl-imidazol-1-yl)-propionaldehyde (1 eq), in THF was added dropwise at room temperature and the mixture was stirred for 1 hour at the same temperature. The mixture was poured into H2O and the whole was extracted with ethyl acetate. The organic layer was washed with NaCl (sat.), dried over sodium sulfate, filtered, and concentrated. To a solution of the residue in ethyl acetate, was added palladium, 10 wt. % on activated carbon and left stirring under 1 atm hydrogen overnight. After the catalyst was filtered off, the filtrate was purified by flash chromatography using a solvent gradient 97% DCM, 3% MeOH, and 0.1% TEA to yield 4-methyl-4-(4-pyridin-3-yl-imidazol-1-yl)pentanoic acid methyl ester (75%). MH+(274)

후처리

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. extractionthe whole was extracted with ethyl acetate
  3. washThe organic layer was washed with NaCl (sat.)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. additionTo a solution of the residue in ethyl acetate, was added palladium, 10 wt. % on activated carbon
  8. waitleft
  9. stirringstirring under 1 atm hydrogen overnight
  10. filtrationAfter the catalyst was filtered off
  11. customthe filtrate was purified by flash chromatography

출처 및 근거

ORD 기록
ord-2703104306094188a0eed0779556293a
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07332476B2

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