Tetrabutylammonium Fluoride → HCID 178488117, compound

HRID 852937Notes

Reaction equation

HRID 852937 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, 3H). 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-b241f22bbe834f40b035d7ebb3ce0b5d
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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