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Trifluoroacetic acid → (3R,3aR,6R,6aR)-6-((6-([1,1'-biphenyl]-4-yl)-3H-imidazo[4,5-c]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

HRID 929258
Notes
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Reaction equation

HRID 929258 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:12]=[CH:11][C:10]3[N:13](COCC[Si](C)(C)C)[C:14]([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:15][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.[OH-].[Na+]>C(Cl)Cl.O>[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:12]=[CH:11][C:10]3[NH:13][C:14]([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:15][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 900423086-([1,1'-biphenyl]-4-yl)-2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine

Product 1

HCID 90067382(3R,3aR,6R,6aR)-6-((6-([1,1'-biphenyl]-4-yl)-3H-imidazo[4,5-c]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents

2
HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To 6-([1,1′-biphenyl]-4-yl)-2-(((3R,3aR,6R,6aS)-6-((tert-butyldimethylsilyl)oxy)hexahydrofuro[3,2-b]furan-3-yl)oxy)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-c]pyridine (26.0 mg, 0.039 mmol) in anhydrous DCM (1.23 mL) was added TFA (0.91 mL, 11.82 mmol). The solution stirred at RT for 52 h. The reaction solution was evaporated under reduced pressure. The residue extracted into EtOAc (35 mL) and washed with 1N NaOH (6.0 mL, 6 mmol) and water (10 mL), dried over Na2SO4, filtered, and evaporated under reduced pressure to afford the title compound. LC-MS: calculated for C24H21N3O4 415.15 observed m/e: 416.16 (M+H)+ (Rt 1.34/2.0 min).

Workup

  1. customThe reaction solution was evaporated under reduced pressure
  2. extractionThe residue extracted into EtOAc (35 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e047c6d338494b1c8b352ed956f686b0
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09290517B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes