2,2-Dimethoxypropane → 5-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione

HRID 728614

反応式

HRID 728614 の反応式
[F:1][C:2]1[C:3](=[O:18])[NH:4][C:5](=[O:17])[N:6]([CH:16]=1)[C@@H:7]1[O:15][C@H:12]([CH2:13][OH:14])[C@@H:10]([OH:11])[C@H:8]1[OH:9].CO[C:21](OC)([CH3:23])[CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>CC(C)=O>[CH3:22][C:21]1([CH3:23])[O:9][CH:8]2[CH:10]([C@@H:12]([CH2:13][OH:14])[O:15][C@H:7]2[N:6]2[C:5](=[O:17])[NH:4][C:3](=[O:18])[C:2]([F:1])=[CH:16]2)[O:11]1

参加物

6

反応物 4

HCID 64952,2-DimethoxypropaneHCID 94275-FluorouridineHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 2008315-fluoro-1-[(4R,6R)-6-(hydroxymethyl)-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]pyrimidine-2,4-dione収率 84%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

In 750 ml of acetone were added 15 g of 5-fluorouridine, 7.5 ml of 2,2-dimethoxypropane and 1.1 g of p-toluenesulfonic acid monohydrate, and the mixture was reacted at room temperature for 4.5 hours under stirring. After allowed to stand overnight at room temperature, 5 g of sodium hydrogen carbonate was added to the reaction mixture and the mixture was stirred at room temperature for 2.5 hours. After insolubles were filtered off, the filtrate was condensed under reduced pressure, and the obtained crystals were recrystallized from ethanol to give 15.7 g (Yield: 84%) of the title compound as colorless needle crystals.

後処理

  1. customthe mixture was reacted at room temperature for 4.5 hours
  2. stirringthe mixture was stirred at room temperature for 2.5 hours
  3. filtrationAfter insolubles were filtered off
  4. customcondensed under reduced pressure
  5. customthe obtained crystals were recrystallized from ethanol

出典と根拠

ORDレコード
ord-b2094df13ded4c48ba4c120b1194933f
出典データセット
uspto-grants-1991_09
特許番号
US05049551

関連ノート

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