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

반응식

HRID 2205186 반응식
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]

참가 물질

5

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

반응 조건

온도
20 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6229a69b08c545c49359192255d7315e
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09370569B2

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