Phosphonic dichloride, (4-chlorophenyl)- → (2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-tetrahydrofuran-3-yl acetate

HRID 2205186

反応式

HRID 2205186 の反応式
ClC1C=CC(P(Cl)(Cl)=O)=CC=1.[NH:12]1C=NN=N1.[C:17]([O:20][C@H:21]1[C@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@:24]([CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH:34]([F:36])[F:35])[O:23][C@H:22]1[N:46]1[CH:51]=[CH:50][C:49](=O)[NH:48][C:47]1=[O:53])(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([O:20][C@H:21]1[C@H:25]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C@:24]([CH2:37][O:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([CH:34]([F:35])[F:36])[O:23][C@H:22]1[N:46]1[CH:51]=[CH:50][C:49]([NH2:12])=[N:48][C:47]1=[O:53])(=[O:19])[CH3:18]

参加物

5

反応物 3

HCID 2724255Phosphonic dichloride, (4-chlorophenyl)-HCID 118294157(2R,3S,4S,5R)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl acetateHCID 178418441HCID 178418441、化合物

生成物 1

HCID 118294215(2R,3S,4S,5R)-2-(4-amino-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5-(benzyloxymethyl)-5-(difluoromethyl)-tetrahydrofuran-3-yl acetate収率 176.3%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
20 °C

実験手順

4-Chlorophenylphosphonic dichloride (0.4 g, 0.81 mmol) was added to a cooled (0° C.) solution of 1-H-tetrazole (0.056 g, 0.81 mmol) and 35 (0.113 g, 0.22 mmol) in dry pyridine (5 mL). The reaction mixture was left to stir under a nitrogen atmosphere at 20° C. for 3 h and then evaporated to dryness under reduced pressure. The residue was dissolved in dioxane and NH3.H2O (5 mL) was added. After stirring for 5 h at 20° C., the reaction mixture was evaporated to dryness under reduced pressure to afford 36 (0.2 g, crude).

後処理

  1. waitThe reaction mixture was left
  2. customevaporated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in dioxane
  4. additionNH3.H2O (5 mL) was added
  5. stirringAfter stirring for 5 h at 20° C.
  6. customthe reaction mixture was evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-6229a69b08c545c49359192255d7315e
出典データセット
uspto-grants-2016_06
特許番号
US09370569B2

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