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Water → N-{2-[2-(3-Oxobutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide

HRID 1661423
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HRID 1661423 반응식
[OH:1][CH:2]([CH3:23])[CH2:3][CH2:4][C:5]1[O:6][C:7]2[C:16]3[CH:15]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13][C:12]=3[CH:11]=[CH:10][C:8]=2[N:9]=1.C[N+]1([O-])CCOCC1.O>C(#N)C>[O:1]=[C:2]([CH3:23])[CH2:3][CH2:4][C:5]1[O:6][C:7]2[C:16]3[CH:15]([CH2:17][CH2:18][NH:19][C:20](=[O:22])[CH3:21])[CH2:14][CH2:13][C:12]=3[CH:11]=[CH:10][C:8]=2[N:9]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 82029Methyl morpholine oxideHCID 57781241N-{2-[2-(3-Hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide

생성물 1

HCID 57781269N-{2-[2-(3-Oxobutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide수율 31%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A suspension of N-{2-[2-(3-hydroxybutyl)-7,8-dihydro-6H-indeno[5,4-d][1,3]oxazol-8-yl]ethyl}acetamide (72.0 mg, 0.228 mmol), 4 Å molecular sieves (72 mg), 4-methylmorpholine N-oxide (66.8 mg, 0.570 mmol) and tetra-n-propylammonium perruthenate(VII) (8.0 mg, 0.0228 mmol) in acetonitrile (3 mL) was stirred at room temperature for 2 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95) and recrystallized (ethyl acetate/hexane) to give the title compound (22.2 mg, yield 31%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate=0/100→5/95)
  6. customrecrystallized (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f342904527c447a089c35254b90e6f95
출처 데이터셋
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08030337B2

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