(Diethylamino)sulfur trifluoride → 1-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

HRID 2205189ノート

反応式

HRID 2205189 の反応式
C(N(S(F)(F)[F:7])CC)C.[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@H:19]1O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C1COCC1>[CH2:10]([O:17][C@@H:18]1[C@:22]([CH2:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH:23]([F:25])[F:24])[O:21][C@@H:20]([N:35]2[CH:40]=[CH:39][C:38](=[O:41])[NH:37][C:36]2=[O:42])[C@@H:19]1[F:7])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

4

反応物 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 1182943391-((2R,3S,4S,5R)-4-(Benzyloxy)-5-((benzyloxy)methyl)-5-(difluoromethyl)-3-hydroxytetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

生成物 1

HCID 1182942631-((2R,3R,4R,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-3-fluoro-tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione収率 46.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

Diethylaminosulfur trifluoride (7.6 g, 47.4 mmol) was added to a suspension of compound 34 (1.5 g, 3.16 mmol) in dry THF (150 mL). The mixture was stirred at 60° C. for 16 h and then cooled to room temperature. The mixture was quenched by the addition of saturated aqueous NaHCO3 solution and then extracted with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Purification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)] afforded 39 as a brown solid (700 mg, 46%). LC-MS (M+H)+=477.4

後処理

  1. temperaturecooled to room temperature
  2. customThe mixture was quenched by the addition of saturated aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness under reduced pressure
  7. customPurification by silica gel chromatography [petroleum ether:ethyl acetate (4:1)]

出典と根拠

ORDレコード
ord-9761056fa149470eb32c13013911d9ca
出典データセット
uspto-grants-2016_06
特許番号
US09370569B2

反応ノート

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