Tetrabutylammonium Fluoride → HCID 178488117, compound

HRID 416257Notes

Reaction equation

HRID 416257 reaction equation
C([Si](C)(C)[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:34])[C:15]1[CH:20]=[CH:19][C:18]([CH2:21][S:22][C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:25]=3[N:24]=2)=[CH:17][CH:16]=1)(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14](=[O:34])[C:15]1[CH:16]=[CH:17][C:18]([CH2:21][S:22][C:23]2[NH:27][C:26]3[CH:28]=[CH:29][C:30]([O:32][CH3:33])=[CH:31][C:25]=3[N:24]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178488118HCID 178488118, compound

Product 1

HCID 178488117HCID 178488117, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of compound 198 (313 mg, 0.600 mmol) in THF (15 ml) was added TBAF 1M in THF (1.20 ml, 1.20 mmol). The reaction mixture was stirred 16 h at room temperature. The solvent was evaporated and the residue was dissolved in EtOAc, washed with sat. NH4Cl and brine, dried over anhydrous MgSO4, filtered and concentrated to afford the title compound 199 (150 mg, 61% yield) as a white powder. 1H NMR (DMSO-d6) δ (ppm): 9.72 (bs, 1H), 9.49 (bs, 1H), 7.90 (d, J=8.1 Hz, 2H), 7.63 (d, J=8.1 Hz, 1H), 7.58 (d, J=8.8 Hz, 2H), 7.51 (d, J=9.5 Hz, 1H), 7.08-6.89 (m, 4H), 6.81 (dd, J=7.0, 7.0 Hz, 1H), 4.76 (s, 2H), 3.81 (s, 3 H). m/z: 406.2 (MH+).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with sat. NH4Cl and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fe296acc8e61420e8e01296d499515ea
Source dataset
uspto-grants-2012_01
Patent number
US08088805B2

Reaction notes

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