Acetic Acid → (3R,5R)-tert-butyl 7-(2,5-diphenyl-4-(pyridin-4-yl)-1H-imidazol-1-yl)-3,5-dihydroxyheptanoate

HRID 350768노트

반응식

HRID 350768 반응식
O=[C:2]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH:3]([NH:10][C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.C(O)(=O)C.[NH2:29][CH2:30][CH2:31][C@H:32]1[O:37]B(C2C=CC=CC=2)[O:35][C@@H:34]([CH2:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:33]1>C(O)C>[C:12]1([C:11]2[N:29]([CH2:30][CH2:31][C@@H:32]([OH:37])[CH2:33][C@@H:34]([OH:35])[CH2:44][C:45]([O:47][C:48]([CH3:49])([CH3:50])[CH3:51])=[O:46])[C:2]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[C:3]([C:4]3[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=3)[N:10]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 11449985t-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetateHCID 21075679N-(2-oxo-2-phenyl-1-(pyridin-4-yl)ethyl)benzamide2회

생성물 1

HCID 58782243(3R,5R)-tert-butyl 7-(2,5-diphenyl-4-(pyridin-4-yl)-1H-imidazol-1-yl)-3,5-dihydroxyheptanoate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of N-(2-oxo-2-phenyl-1-(pyridin-4-yl)ethyl)benzamide, 67 (1.6 g) and acetic acid (1.5 mL) in ethanol (50 mL) is added tert-butyl 2-((4R,6R)-6-(2-aminoethyl)-2-phenyl-1,3,2-dioxaborinan-4-yl)acetate (7.9 g). Upon heating under reflux for 16 h, the solution is cooled to room temperature and the solvent is evaporated. The residue is partitioned between saturated aqueous sodium hydrogen carbonate and dichloromethane, the layers separated and the organic phase washed with brine, dried (magnesium sulfate), filtered and concentrated. Purification of the residue via chromatography affords the title compound, 68 (0.35 g).

후처리

  1. temperatureUpon heating
  2. temperatureunder reflux for 16 h
  3. customthe solvent is evaporated
  4. customThe residue is partitioned between saturated aqueous sodium hydrogen carbonate and dichloromethane
  5. customthe layers separated
  6. washthe organic phase washed with brine
  7. dry with materialdried (magnesium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification of the residue via chromatography

출처 및 근거

ORD 기록
ord-b3a693da2103488bb75e48c81af2a8ff
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183285B2

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