Trimethylsilyl triflate → (2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate

HRID 1700096노트

반응식

HRID 1700096 반응식
Cl.[C:2]1([CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9][NH:10][C:11]2[N:19]=[C:18]([CH2:20][NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23])[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C@@H:39]1[O:51][C@H:50]([CH2:52][O:53][C:54](=[O:56])[CH3:55])[C@@H:45]([O:46][C:47](=[O:49])[CH3:48])[C@H:40]1[O:41][C:42](=[O:44])[CH3:43])(=O)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C>ClC(Cl)(Cl)C.C(OCC)(=O)C>[C:47]([O:46][C@H:45]1[C@@H:40]([O:41][C:42](=[O:44])[CH3:43])[C@H:39]([N:15]2[CH:14]=[N:13][C:12]3[C:16]2=[N:17][C:18]([CH2:20][NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:23])=[O:24])=[N:19][C:11]=3[NH:10][CH2:9][CH:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[O:51][C@@H:50]1[CH2:52][O:53][C:54](=[O:56])[CH3:55])(=[O:49])[CH3:48]

참가 물질

6

반응물 3

HCID 65367Trimethylsilyl triflateHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 178455636HCID 178455636, 화합물

생성물 1

HCID 69972041(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy) methyl]-5-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulfonyl)amino]methyl}-9H-purin-9-yl)tetrahydro-3-furanyl acetate

시약·촉매·용매 2

HCID 62781,1,1-Trichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of N-({6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulfonamide hydrochloride (Preparation 8) (0.21 g, 0.42 mmol) in 1,1,1-trichloroethane (10 ml) was treated with N,O-bis(trimethylacetamide) (0.6 ml, 2.45 mmol) and the mixture was heated under reflux for 2 hours. The solvent was removed under reduced pressure and the residue was azeotroped with toluene (×2). The residue was dissolved in toluene (10 ml) and treated with the β-D-ribofuranose-1,2,3,5-tetraacetate (0.16 g, 0.50 mmol) and trimethylsilyltriflate (0.1 ml, 0.5 mmol). The mixture was then heated at reflux for 4 hours. The mixture was diluted with ethyl acetate, washed sequentially with saturated aqueous sodium hydrogen carbonate solution and brine and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2 by volume) gradually changing to dichloromethane:methanol (95:5 by volume) to afford the title compound as a 1:3 mixture of α-and β-anomers (188 mg).

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was azeotroped with toluene (×2)
  5. dissolutionThe residue was dissolved in toluene (10 ml)
  6. temperatureThe mixture was then heated
  7. temperatureat reflux for 4 hours
  8. washwashed sequentially with saturated aqueous sodium hydrogen carbonate solution and brine
  9. customevaporated under reduced pressure
  10. customThe residue was purified by column chromatography on silica gel eluting with a gradient system of dichloromethane:methanol (98:2 by volume)

출처 및 근거

ORD 기록
ord-2499fbfdff40461fb2c01677042ad89b
출처 데이터셋
uspto-grants-2002_02
특허 번호
US06350735B1

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