Trifluoroacetic acid → (3R,3aR,6R,6aR)-6-((2-([1,1'-biphenyl]-4-yl)-7H-purin-8-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 929260노트

반응식

HRID 929260 반응식
[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:15]=[C:14]3[C:10]([N:11](COCC[Si](C)(C)C)[C:12]([O:16][C@@H:17]4[CH2:21][O:20][C@@H:19]5[C@H:22]([O:25][Si](C(C)(C)C)(C)C)[CH2:23][O:24][C@H:18]45)=[N:13]3)=[CH:9][N:8]=2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+].CCOC(C)=O>C(Cl)Cl>[C:1]1([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:6]=[CH:5][C:4]([C:7]2[N:15]=[C:14]3[C:10]([NH:11][C:12]([O:16][C@H:17]4[C@H:18]5[O:24][CH2:23][C@@H:22]([OH:25])[C@H:19]5[O:20][CH2:21]4)=[N:13]3)=[CH:9][N:8]=2)=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 900419412-([1,1'-biphenyl]-4-yl)-8-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine

생성물 1

HCID 90067461(3R,3aR,6R,6aR)-6-((2-([1,1'-biphenyl]-4-yl)-7H-purin-8-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 2-([1,1′-biphenyl]-4-yl)-8-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-purine (38.0 mg, 0.057 mmol) in anhydrous DCM (1.8 mL) was added TFA (1.33 mL, 17.25 mmol). The solution stirred at RT for 22 h. The reaction solution cooled to 0° C. and 1N NaOH (18.2 mL, 18.2 mmol) and EtOAc (60 mL) added. The organic layer washed with brine (20 mL), dried over Na2SO4, filtered, and evaporated under reduced pressure. Flash chromatography utilizing a 12 g silica RediSep Rf® Gold column and employing a 0-15% MeOH/DCM gradient afforded the title compound. LC-MS: calculated for C23H20N4O4 416.15 observed m/e: 417.36 (M+H)+ (Rt 0.93/2.0 min).

후처리

  1. temperatureThe reaction solution cooled to 0° C.
  2. washThe organic layer washed with brine (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b1aa019b37c445a09a2ec32a9e39ca28
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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