Tetrabutylammonium Fluoride → HCID 59558768, compound

HRID 1024884Notes

Reaction equation

HRID 1024884 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:24][CH2:23][CH2:22]2)(=[O:20])=[O:19])[CH:14]=[C:13]([O:25][C@H:26]([CH2:36][O:37][CH2:38][CH3:39])[CH2:27][O:28][Si](C(C)(C)C)(C)C)[N:12]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.O>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([N:21]2[CH2:22][CH2:23][CH2:24]2)(=[O:19])=[O:20])[CH:14]=[C:13]([O:25][C@@H:26]([CH2:27][OH:28])[CH2:36][O:37][CH2:38][CH3:39])[N:12]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53628355HCID 53628355, compound

Product 1

HCID 59558768HCID 59558768, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(ethoxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide, (product from step v) (0.79 g) in THF (10 mL) was added a 1M solution of tetrabutylammoniumfluoride in THF (2.4 mL) with stirring, at ambient temperature, for 72 h. The reaction mixture was diluted with H2O and extracted with EtOAc (×2). The organic layer was washed with H2O then brine and dried (MgSO4), filtered and evaporated. The resulting oil was purified by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase) then titurated with DCM followed by ether/iso-hexane to give the title compound as a white solid. Yield: 0.28 g

Workup

  1. extractionextracted with EtOAc (×2)
  2. washThe organic layer was washed with H2O
  3. dry with materialbrine and dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting oil was purified by reverse phase HPLC (symmetry as the stationary phase and TFA/acetonitrile as the mobile phase)

Sources & evidence

ORD record
ord-d5f9a8a140d7456d91dcf2f340632adc
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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