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

HRID 929254Notes

Reaction equation

HRID 929254 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:15](COCC[Si](C)(C)C)[C:14]([O:24][C@H:25]3[C@H:29]4[O:30][CH2:31][C@@H:32]([OH:33])[C@H:28]4[O:27][CH2:26]3)=[N:13][C:5]2=[N:6][C:7]=1[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[NH:15][C:14]([O:24][C@H:25]3[C@H:29]4[O:30][CH2:31][C@@H:32]([OH:33])[C@H:28]4[O:27][CH2:26]3)=[N:13][C:5]2=[N:6][C:7]=1[C:8]1[CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90042471(3R,3aR,6R,6aR)-6-((6-chloro-5-(cyclopent-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 90067193(3R,3aR,6R,6aR)-6-((6-chloro-5-(cyclopent-1-en-1-yl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (3R,3aR,6R,6aR)-6-((6-chloro-5-(cyclopent-1-en-1-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol (15 mg, 0.030 mmol) in anhydrous DCM (0.55 mL) was added TFA (0.55 mL, 7.13 mmol). The solution stirred at RT for 54 h. The reaction solution was evaporated under reduced pressure. Flash chromatography utilizing a 4 g silica RediSep Rf® Gold column and employing a 0-20% (1% NH4OH in MeOH)/DCM gradient afforded the title compound. LC-MS: calculated for C17H18ClN3O4 363.10 observed m/e: 364.11 (M+H)+ (Rt 1.20/2.0 min).

Workup

  1. customThe reaction solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7416ef8e1921435d8a3d3edd5a666fd3
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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