Water → HCID 178455377, compound

HRID 715566Notes

Reaction equation

HRID 715566 reaction equation
[N:1]([C@@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3[N:21]=[C:20]4[N:22]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:23]([O:25][C@@H:26]5[CH2:30][O:29][C@@H:28]6[C@H:31]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH2:32][O:33][C@H:27]56)=[N:24][C:19]4=[CH:18][C:17]=3[Cl:50])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[Si:35]([O:34][C@H:31]1[C@H:28]2[O:29][CH2:30][C@@H:26]([O:25][C:23]3[N:22]([CH2:42][O:43][CH2:44][CH2:45][Si:46]([CH3:49])([CH3:48])[CH3:47])[C:20]4=[N:21][C:16]([C:13]5[CH:14]=[CH:15][C:10]([C@@H:7]6[CH2:8][CH2:9][C@H:4]([NH2:1])[CH2:5][CH2:6]6)=[CH:11][CH:12]=5)=[C:17]([Cl:50])[CH:18]=[C:19]4[N:24]=3)[C@H:27]2[O:33][CH2:32]1)([C:38]([CH3:40])([CH3:41])[CH3:39])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 178455383HCID 178455383, compound

Product 1

HCID 178455377HCID 178455377, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

5-(4-((cis)-4-Azidocyclohexyl)phenyl)-2-((3R,3aR,6R,6aS)-6-(tert-butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridine (210 mg) is dissolved in tetrahydrofurane (1 mL) treated with triphenylphosphine (90 mg) and stirred for 4 hours at room temperature and for 12 hours at 40° C. Water (220 μL) is added and the mixture is stirred for further 12 hours at 80° C. Then the mixture is partitioned between hydrochloric acid (1 M) and diethylether. The organic phase is washed with aqueous NaOH solution (1 M), dried (MgSO4) and concentrated. The residue is chromatographed over aluminium oxide (ethyl acetate/methanol 100:0→0:100) to give the title compound. LC (method 4): tR=0.61 min; Mass spectrum (ESI+): m/z=715 [M+H]+.

Workup

  1. stirringthe mixture is stirred for further 12 hours at 80° C
  2. customThen the mixture is partitioned between hydrochloric acid (1 M) and diethylether
  3. washThe organic phase is washed with aqueous NaOH solution (1 M)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe residue is chromatographed over aluminium oxide (ethyl acetate/methanol 100:0→0:100)

Sources & evidence

ORD record
ord-618f2df8c3b14168ad8ec8f043436511
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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