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Ammonium Acetate → 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridine

HRID 1882012
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HRID 1882012 반응식
[Si:1]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17](=O)[CH:18]([CH3:42])[CH2:19][C:20](=O)[CH:21]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH:38]3[CH2:40][CH2:39]3)(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:15][CH:16]=1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:48]>C(O)(=O)C.C(OCC)(=O)C>[Si:1]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:48][C:20]([CH:21]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH:38]4[CH2:40][CH2:39]4)(=[O:37])=[O:36])=[CH:31][CH:30]=3)[CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:19][C:18]=2[CH3:42])=[N:15][CH:16]=1)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]
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참가 물질

5

반응물 2

HCID 517165Ammonium AcetateHCID 593312241-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

생성물 1

HCID 593315955-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridine수율 74.5%

시약·촉매·용매 2

HCID 176
Acetic Acid
용매
HCID 8857Ethyl Acetate용매

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온도
90 °C

실험 절차

To a solution of 1-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (180 mg) in acetic acid (5 mL) was added ammonium acetate (354 mg), and the mixture was stirred at 90° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (130 mg, yield 74%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 609 (MH+).

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c2fe33127fc0499fbff0adfd40cdfebb
출처 데이터셋
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08318746B2

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