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Lithium Hydroxide → {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid

HRID 536024
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인쇄 미리보기

반응식

HRID 536024 반응식
C([O:3][C:4](=[O:36])[CH2:5][NH:6][C:7]1[N:8]([CH2:33][CH2:34][CH3:35])[C:9](=[O:32])[C:10]2[NH:11][C:12]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:20]=3)=[N:13][C:14]=2[N:15]=1)C.[OH-].[Li+]>C1COCC1.CO.O>[O:32]=[C:9]1[N:8]([CH2:33][CH2:34][CH3:35])[C:7]([NH:6][CH2:5][C:4]([OH:36])=[O:3])=[N:15][C:14]2[N:13]=[C:12]([C:16]3[CH:17]=[N:18][N:19]([CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=4)[CH:20]=3)[NH:11][C:10]1=2
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참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 67135287{6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester

생성물 1

HCID 67134944{6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid수율 46%

시약·촉매·용매 3

HCID 887Methanol용매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid ethyl ester in THF (2 ml), MeOH (1 ml) and Water (1 ml) was added lithium hydroxide (0.02 g, 0.476 mmol) at 0° C. The reaction mixture was stirred at room temperature for overnight. The reaction mixture was concentrated and water was added. It was extracted with ethyl acetate. Ethyl acetate layer was washed with water and brine. Ethyl acetate layer was dried over sodium sulphate, filtered and concentrated under reduced pressure and the residue obtained was purified by column chromatography to obtain {6-Oxo-1-propyl-8-[1-(3-trifluoromethyl-benzyl)-1H-pyrazol-4-yl]-6,7-dihydro-1H-purin-2-ylamino}-acetic acid (0.035 g, 46%) as a yellow solid.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additionwater was added
  3. extractionIt was extracted with ethyl acetate
  4. washEthyl acetate layer was washed with water and brine
  5. dry with materialEthyl acetate layer was dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue obtained
  9. customwas purified by column chromatography

출처 및 근거

ORD 기록
ord-b1033486d50f4ca3959e9707084c88f3
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08859566B2

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