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Potassium Carbonate → Oxiracetam

HRID 2291685
ノート
印刷プレビュー

反応式

HRID 2291685 の反応式
Cl.CC(C1[NH:9][C:8](=[O:10])[CH2:7][NH:6]1)C.N1C2(CCCCC2)NCC1=O.C(=O)([O-])[O-].[K+].[K+].[O:28]1[CH2:36][CH:29]1[CH2:30][C:31]([O:33]CC)=O>O.CN(C=O)C.CC(C)=O>[CH2:30]1[C:31](=[O:33])[N:6]([CH2:7][C:8]([NH2:9])=[O:10])[CH2:36][CH:29]1[OH:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 11430Potassium CarbonateHCID 9898830Ethyl 2-(oxiran-2-yl)acetateHCID 131250391,4-Diazaspiro[4.5]decan-2-oneHCID 212792932-(1-Methylethyl)-4-imidazolidinone hydrochloride

生成物 1

HCID 4626Oxiracetam収率 6.8%

試薬・触媒・溶媒 3

HCID 180Acetone
溶媒
HCID 962Water溶媒2 回
HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

5.8 g of 2-(1-methylethyl)-4-imidazolidinone hydrochloride ((5); R4 =H, R5 =isopropyl) (0.035 moles) are shaken in 10 ml water and treated with 2.4 g potassium carbonate (0.0174 moles). 4.5 g ethyl 3,4-epoxybutanoate and 6 ml acetone are added, and stirring is maintained for 45 h at 70° C. After evaporation, the residue is chromatographed on silica, eluting with 8:2 ethyl acetate/methanol. The main fractions are collected and evaporated. The oil that remains is taken up with ethyl acetate. After being left to stand overnight the white compound obtained is filtered: 1.3 g ethyl 2-(1-methylethyl)-4-oxo-1-imidazolidine-β-hydroxybutanoate m.p. 118°-122° C. 0.95 g of this compound (3.7 mmoles) are heated to boiling for 15 h in 4 ml DMF and 1 ml water. After evaporation in vacuo, the residue is taken up with methanol, and the solution is filtered. 0.37 g oxiracetam is obtained as a white crystalline powder, m.p. 167°-70° C. (63.2%).

後処理

  1. customAfter evaporation
  2. customthe residue is chromatographed on silica
  3. washeluting with 8:2 ethyl acetate/methanol
  4. customThe main fractions are collected
  5. customevaporated
  6. waitAfter being left
  7. customthe white compound obtained
  8. filtrationis filtered
  9. customAfter evaporation in vacuo
  10. filtrationthe solution is filtered

出典と根拠

ORDレコード
ord-433dbce7844045909b2be15176cc5b83
出典データセット
uspto-grants-1989_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04797496

反応ノート

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