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

반응식

HRID 728614 반응식
[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

참가 물질

6

반응물 4

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

생성물 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-dione수율 84%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b2094df13ded4c48ba4c120b1194933f
출처 데이터셋
uspto-grants-1991_09
특허 번호
US05049551

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