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

HRID 431690ノート

反応式

HRID 431690 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

反応条件

温度
50 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-382aacc162bc455e98f957278a729e8c
出典データセット
uspto-grants-2003_12
特許番号
US06660740B1

反応ノート

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