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Tetrahydrofuran → HCID 11236657, 화합물

HRID 2422170
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HRID 2422170 반응식
C1COCC1.[Cl:6][C:7]1[C:12]([CH2:13][C:14]([O:16]C)=[O:15])=[C:11]([Cl:18])[N:10]=[C:9]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)=[O:28])=[CH:22][CH:21]=2)[N:8]=1.[OH-].[Na+]>O>[Cl:18][C:11]1[C:12]([CH2:13][C:14]([OH:16])=[O:15])=[C:7]([Cl:6])[N:8]=[C:9]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:27]([C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=3)=[O:28])=[CH:24][CH:25]=2)[N:10]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 59514514HCID 59514514, 화합물

생성물 1

HCID 11236657HCID 11236657, 화합물수율 15%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A THF (1.5 mL) solution of methyl {4,6-dichloro-2-[4-(2-naphthoylamino)benzyl]pyrimidin-5-yl}acetate (0.048 g, 0.10 mmol) at room temperature was treated with 1N NaOH (1 mL). After stirring for 16 hours at room temperature, the reaction mixture was poured into water and washed with EtOAc. The aqueous layer was acidified with 1N HCl and back extracted with EtOAc. The combined organic extracts was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The remaining residue was chromatographed over silica gel eluting with 10% THF in CH2Cl2 containing 0.5% AcOH to give {4,6-dichloro-2-[4-(2-naphthoyl-amino)benzyl]pyrimidin-5-yl}acetic acid (0.007 g, 15% yield) as a white solid.

후처리

  1. washwashed with EtOAc
  2. extractionback extracted with EtOAc
  3. washThe combined organic extracts was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe remaining residue was chromatographed over silica gel eluting with 10% THF in CH2Cl2 containing 0.5% AcOH

출처 및 근거

ORD 기록
ord-4c0a365b297b42d9838dab89d18540a0
출처 데이터셋
uspto-grants-2011_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07960393B2

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