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Triacetoxyperiodinane → Ethyl oxo[(2-oxopropyl)amino]acetate

HRID 2200583
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HRID 2200583 반응식
[OH:1][CH:2]([CH3:12])[CH2:3][NH:4][C:5](=[O:11])[C:6]([O:8][CH2:9][CH3:10])=[O:7].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[O:11]=[C:5]([NH:4][CH2:3][C:2](=[O:1])[CH3:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7]
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참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 85994322Ethyl 2-(2-hydroxypropylamino)-2-oxo-acetate

생성물 1

HCID 57348900Ethyl oxo[(2-oxopropyl)amino]acetate수율 81.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of ethyl 2-(2-hydroxypropylamino)-2-oxoacetate (2.1 g, 13 mmol) in DCM (30 mL) was added Dess-Martin periodinane (6.2 g, 14.6 mmol) in portions at 0° C. and the resulting mixture was stirred at room temperature for 16 h. The reaction was diluted with DCM and extracted with saturated aqueous sodium bicarbonate solution and brine. The organic layer was dried and concentrated to give crude product, which was purified via silica gel chromatography eluting with DCM/methanol (60:1) to give ethyl 2-oxo-2-(2-oxopropylamino)acetate (1.7 g, 81.2% yield) as yellow syrup. LCMS retention time 0.392 min, LCMS MH+ 174.

후처리

  1. extractionextracted with saturated aqueous sodium bicarbonate solution and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customto give crude product, which
  5. customwas purified via silica gel chromatography
  6. washeluting with DCM/methanol (60:1)

출처 및 근거

ORD 기록
ord-63cc3d2ea4cd43f5bf266711f361120a
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359359B2

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