Tetrabutylammonium Fluoride → HCID 69475822, compound

HRID 339608Notes

Reaction equation

HRID 339608 reaction equation
[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32][O:33][Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:9][C@H:10]1[C@H:14]([F:15])[C@H:13]([N:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:30])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:18][C:17]2=[O:31])[O:12][C@@H:11]1[CH2:32][OH:33])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69478080HCID 69478080, compound

Product 1

HCID 69475822HCID 69475822, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 2 (0.64 g, 0.92 mmol) in 10.0 mL of anhydrous THF was added TBAF (1.20 mL, 1.0 M in THF) at 0° C. The resulting solution was stirred for 6 h at rt. The solvent was removed under reduced pressure and the residue was purified on silica gel column chromatography (Hexane:EtOAc=4:1 to 1:1 v/v) to give compound 3 (0.39 g, 0.85 mmol) in 93% yield. 1H NMR (CD3OD, 400 MHz) δ 8.58 (d, J=7.6, 1H), 8.00 (m, 4H), 7.63 (m, 3H), 7.51 (m, 4H), 6.16 (dd, J=17.6, 1.6, 1H), 5.55 (dd, J=4.4, 1.6, 0.5H), 5.47 (m, 1H), 5.42 (dd, J=4.4, 1.6, 0.5H), 4.51 (m, 1H), 4.06 (dd, J=12.8, 2.4, 1H), 3.86 (dd, J=12.8, 3.2, 1H); MS calcd for C23H20FN3O6 m/z 454.1 (M+H)+, found 454.2.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified on silica gel column chromatography (Hexane:EtOAc=4:1 to 1:1 v/v)

Sources & evidence

ORD record
ord-3d54da2207c2470db6441cee7dd46c91
Source dataset
uspto-grants-2014_11
Patent number
US08895531B2

Reaction notes

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