Dimethyl Carbonate → T-1095

HRID 1003940노트

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HRID 1003940 반응식
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([OH:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][OH:33])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2.[C:34](=O)([O:37]C)[O:35][CH3:36]>COCCOC.C(Cl)(Cl)Cl>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([CH2:10][CH2:11][C:12]([C:14]3[C:19]([OH:20])=[CH:18][C:17]([CH3:21])=[CH:16][C:15]=3[O:22][C@@H:23]3[O:31][C@H:30]([CH2:32][O:33][C:34]([O:35][CH3:36])=[O:37])[C@@H:28]([OH:29])[C@H:26]([OH:27])[C@H:24]3[OH:25])=[O:13])[CH:8]=[CH:9][C:2]1=2

참가 물질

5

반응물 2

HCID 12021Dimethyl CarbonateHCID 6918439T-1095A

생성물 1

HCID 6918410T-1095

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 80711,2-Dimethoxyethane용매

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온도
40 °C

실험 절차

3-(5-Benzo[b]furanyl)-2'-(β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (10 g) is dissolved in ethyleneglycol dimethyl ether (30 ml), and thereto are added dimethyl carbonate (100 ml), Novozyme 435 (2 g, manufactured by Novo Nordisk A/S, Denmark) and molecular sieves 4A powder (8 g), and the mixture is stirred at 40° C. for 24 hours, and stirred at room temperature for 14 hours. The reaction mixture is diluted with chloroform, and the insoluble materials are removed by filtration. The filtrate is concentrated to dryness, and the residue is dissolved in ethyl acetate. The mixture is washed successively with 10% aqueous hydrochloric acid, water, a saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried, and concentrated under reduced pressure. The residue is recrystallized three times from ether-isopropyl ether-water to give 3-(5-benzo[b]-furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-hydroxy-4'-methylpropiophenone (7.9 g). The physicochemical properties of the compound are the same as those of the compound obtained in Example 18.

후처리

  1. stirringstirred at room temperature for 14 hours
  2. customthe insoluble materials are removed by filtration
  3. concentrationThe filtrate is concentrated to dryness
  4. dissolutionthe residue is dissolved in ethyl acetate
  5. washThe mixture is washed successively with 10% aqueous hydrochloric acid, water
  6. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated aqueous sodium chloride solution, dried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue is recrystallized three times from ether-isopropyl ether-water

출처 및 근거

ORD 기록
ord-16f19303bf8f4f6faf5401dca756d805
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06048842

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