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

HRID 586206ノート

反応式

HRID 586206 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 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).

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-c565d679c5b847fe836890f1435a83cf
出典データセット
uspto-grants-2005_08
特許番号
US06936600B2

反応ノート

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