HCID 86607298, 화합물 → HCID 86607329, 화합물

HRID 552755노트

반응식

HRID 552755 반응식
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]2[C@@H:13]([O:14][Si](C(C)C)(C(C)C)O[Si](C(C)C)(C(C)C)[O:18][CH2:19]2)[C@@H:12]1[O:34][CH3:35]>C1COCC1.N1C=CC=CC=1.F.N1C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:21][C@H:20]([CH2:19][OH:18])[C@@H:13]([OH:14])[C@@H:12]1[O:34][CH3:35]

참가 물질

6

반응물 1

HCID 86607298HCID 86607298, 화합물

생성물 1

HCID 86607329HCID 86607329, 화합물수율 95.2%

시약·촉매·용매 4

HCID 14917Hydrofluoric Acid촉매HCID 1049Pyridine용매HCID 8857Ethyl Acetate용매HCID 16069498Pyridine tetrahydrofuran용매

실험 절차

To a solution of 6-chloro-9-[(6aR,8R,9S,9aR)-2,2,4,4-tetraisopropyl-9-methoxytetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl]-9H-purine (1.31 g, 2.41 mmol) in THF/pyridine (12 mL, 1:1) was added approximately 20 drops of hydrofluoric acid in pyridine. This solution was stirred at r.t. overnight. The reaction was diluted with EtOAc (10 mL) and quenched with saturated aq NaHCO3. The aq layer was extracted with EtOAc (3×40 mL) and the combined organics were dried (Na2SO4), filtered, and concentrated. The crude material was purified by flash chromatography (0 to 10% MeOH/DCM) to afford the title compound (0.690 g, 74%).

후처리

  1. customquenched with saturated aq NaHCO3
  2. extractionThe aq layer was extracted with EtOAc (3×40 mL)
  3. dry with materialthe combined organics were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified by flash chromatography (0 to 10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-ae290d9c4ccc44ac9bd955fc5dc43218
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951810B2

반응 노트

불러오는 중…