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

HRID 929174Notes

Reaction equation

HRID 929174 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[CH:10]=[C:11]2[N:18](COCC[Si](C)(C)C)[C:17]([O:27][C@H:28]3[C@H:32]4[O:33][CH2:34][C@@H:35]([OH:36])[C@H:31]4[O:30][CH2:29]3)=[N:16][C:12]2=[N:13][C:14]=1[I:15].CO>ClCCl>[Cl:8][C:9]1[CH:10]=[C:11]2[NH:18][C:17]([O:27][C@H:28]3[C@H:32]4[O:33][CH2:34][C@@H:35]([OH:36])[C@H:31]4[O:30][CH2:29]3)=[N:16][C:12]2=[N:13][C:14]=1[I:15]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 90042470(3R,3aR,6R,6aR)-6-((6-chloro-5-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Product 1

HCID 90042050(3R,3aR,6R,6aR)-6-((6-chloro-5-iodo-1H-imidazo[4,5-b]pyridin-2-yl)oxy)hexahydrofuro[3,2-b]furan-3-ol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic acid (70.0 ml, 909 mmol) was added to a stirred solution of (3R,3aR,6R,6aR)-6-[6-chloro-5-iodo-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]oxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-3-ol (14.99 g, 27.1 mmol) in dichloromethane (70 ml). The reaction mixture was an amber solution that was stirred at room temperature. After 3 hours, the reaction mixture was concentrated under reduced pressure to give an amber oil. Methanol (50 ml) was added and the resulting solution was stirred at room temperature. After about 5 minutes, the product crystallized and precipitated to give a white suspension. Dichloromethane (50 ml) was added to the reaction mixture. The crystalline product was collected from the reaction mixture by vacuum filtration and was dried overnight under vacuum to give the title compound as a crystalline white solid. LC-MS: calculated for C12H11ClIN3O4 422.95 observed m/e: 424.0 (M+H)+ (Rt 0.92/2 min).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customto give an amber oil
  3. stirringthe resulting solution was stirred at room temperature
  4. waitAfter about 5 minutes
  5. customthe product crystallized
  6. customprecipitated
  7. customto give a white suspension
  8. filtrationThe crystalline product was collected from the reaction mixture by vacuum filtration
  9. customwas dried overnight under vacuum

Sources & evidence

ORD record
ord-fe9353f2a92e401aa0e5402c250e6a27
Source dataset
uspto-grants-2016_03
Patent number
US09290517B2

Reaction notes

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