Vinyl Acetate → (R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one

HRID 586206노트

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HRID 586206 반응식
[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].OC([C:10]1[NH:15][C:14](=[O:16])[CH:13]=[CH:12][N:11]=1)C>O1CCOCC1>[C:1]([O:4][C@@H:5]([C:10]1[NH:15][C:14](=[O:16])[CH:13]=[CH:12][N:11]=1)[CH3:6])(=[O:3])[CH3:2]

참가 물질

4

반응물 2

HCID 7904Vinyl AcetateHCID 110189492-(1-hydroxyethyl)pyrimidin-4(3H)-one

생성물 1

HCID 11105982(R)-2-(1-Acetoxy-ethyl)-3H-pyrimidin-4-one

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
50 °C

실험 절차

To a solution of vinyl acetate (4.3 g, 50 mmol) in dioxane (63 mL) was added 2-(1-hydroxy-ethyl)-3H-pyrimidin-4-one (prepared according to the method of Preparation Twelve, 2.1 g, 15.1 mmol), and the mixture was heated to 50° C. To the resulting solution was added lipase P30 (0.21 g, 10 wt %) and the heating was continued for 24 h. The reaction mixture was filtered and the filtrate was evaporated to obtain a thick syrupy liquid residue. The residue was purified by flash column chromatography (95:5 dichloromethane:methanol) to give the title compound as a colorless liquid, 0.97 g (92% of theory). 1H NMR (CDCl3, 300 MHz) δ 1.61 (d, 3H), 2.20 (s, 3H), 5.65 (q, 1H), 6.35 (d, 1H), 7.97 (d, 1H), 11.94 (s, 1H); [α]D+39.9 (c 1.0, MeOH).

후처리

  1. customprepared
  2. customaccording to the method of Preparation Twelve, 2.1 g, 15.1 mmol), and the mixture
  3. additionTo the resulting solution was added lipase
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate was evaporated
  6. customto obtain a thick syrupy liquid residue
  7. customThe residue was purified by flash column chromatography (95:5 dichloromethane:methanol)

출처 및 근거

ORD 기록
ord-c565d679c5b847fe836890f1435a83cf
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936600B2

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