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Water → N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

HRID 2277330
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HRID 2277330 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][C:16]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])[N:19]=[CH:18][C:17]=3[N:30]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][CH:11]([OH:13])[CH3:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:14]2[O:15][C:16]3[CH:21]=[C:20]([O:22][CH2:23][C@@H:24]([NH:26][C:27](=[O:29])[CH3:28])[CH3:25])[N:19]=[CH:18][C:17]=3[N:30]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][C:11](=[O:13])[CH3:12]
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6

반응물 4

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86731420N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide

생성물 1

HCID 86731421N-((2S)-1-((2-(3-fluoro-4-(3-oxobutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide수율 55.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of N-((2S)-1-((2-(3-fluoro-4-(3-hydroxybutoxy)phenyl)[1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)acetamide (300 mg) and Dess-Martin reagent (914 mg) in DMF (30 mL) was stirred at room temperature for 15 hr. To the mixture was added saturated aqueous sodium thiosulfate solution, and the mixture was stirred at room temperature for 10 min. Water was added thereto, and the mixture was extracted with ethyl acetate. The combined organic layer were washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol) to give the title compound (165 mg).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe combined organic layer were washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)

출처 및 근거

ORD 기록
ord-2d26735c50a143d5873dcbdfa00d81fb
출처 데이터셋
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09133129B2

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