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Potassium Carbonate → Methyl 2-(1-methylethyl)-4-oxoimidazolidine beta-hydroxybutanoate

HRID 2291687
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HRID 2291687 반응식
Cl.[CH3:2][CH:3]([CH:5]1[NH:9][C:8](=[O:10])[CH2:7][NH:6]1)[CH3:4].N1C2(CCCCC2)NC[C:12]1=O.C(=O)([O-])[O-].[K+].[K+].[O:28]1[CH2:35][CH:29]1[CH2:30][C:31]([O:33]C)=[O:32]>CC(C)=O.O>[CH3:12][N:6]1[CH2:7][C:8](=[O:10])[NH:9][CH:5]1[CH:3]([CH3:4])[CH3:2].[OH:28][CH:29]([CH3:35])[CH2:30][C:31]([O-:33])=[O:32]
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참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 107294Methyl 3,4-epoxybutyrateHCID 131250391,4-Diazaspiro[4.5]decan-2-oneHCID 212792932-(1-Methylethyl)-4-imidazolidinone hydrochloride

생성물 1

HCID 86742668Methyl 2-(1-methylethyl)-4-oxoimidazolidine beta-hydroxybutanoate

시약·촉매·용매 2

HCID 180
Acetone
용매
HCID 962Water용매

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온도
70 °C

실험 절차

12 g 2-(1-methylethyl)-4-imidazolidinone hydrochloride ((5); R4 =H, R5 =isopropyl) (0.073 moles) are shaken with 20 ml water and treated with 5 g potassium carbonate (0.036 moles). 8.5 g methyl 3,4-epoxybutanoate (0.073 moles) and 12 ml acetone are added. The mixture is stirred for 45 h at 70° C. After evaporating, the residue is chromatographed on silica, eluting with 8:2 ethyl acetate/methanol. The main fractions are combined and evaporated. 2.5 g of methyl 2-(1-methylethyl)-4-oxoimidazolidine-β-hydroxybutanoate, m.p. 109°-122° C., are obtained as a white powder (14.4%). 2.0 g of this compound (0.0082 mole) are heated to boiling for 15 h with 8.8 ml DMF and 2.2 ml water. After evaporation in vacuo, the residue is taken up with methanol, and filtered. 0.74 g oxiracetam is obtained as a white crystalline powder, m.p. 167°-70° C. (57.4%).

후처리

  1. customAfter evaporating
  2. customthe residue is chromatographed on silica
  3. washeluting with 8:2 ethyl acetate/methanol
  4. customevaporated

출처 및 근거

ORD 기록
ord-9696946bae50456798d9a93b03bae61c
출처 데이터셋
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04797496

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