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

HRID 431690노트

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HRID 431690 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 9,10 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-382aacc162bc455e98f957278a729e8c
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06660740B1

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