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 929260Notes

Reaction equation

HRID 929260 reaction equation
[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

Participants

6

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-b1aa019b37c445a09a2ec32a9e39ca28
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

Loading…