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 929260ノート

反応式

HRID 929260 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b1aa019b37c445a09a2ec32a9e39ca28
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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