Tetrabutylammonium Fluoride → HCID 86696263, compound

HRID 2175145Notes

Reaction equation

HRID 2175145 reaction equation
[Si]([O:8][CH2:9][CH2:10][NH:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][C:18]([S:22][C:23]1[N:27]3[CH:28]=[C:29]([C:32]4[CH:33]=[N:34][N:35]([CH3:37])[CH:36]=4)[CH:30]=[CH:31][C:26]3=[N:25][N:24]=1)=[CH:17][CH:16]=2)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:37][N:35]1[CH:36]=[C:32]([C:29]2[CH:30]=[CH:31][C:26]3[N:27]([C:23]([S:22][C:18]4[CH:19]=[C:20]5[C:15](=[CH:16][CH:17]=4)[N:14]=[CH:13][C:12]([NH:11][CH2:10][CH2:9][OH:8])=[CH:21]5)=[N:24][N:25]=3)[CH:28]=2)[CH:33]=[N:34]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86696264HCID 86696264, compound

Product 1

HCID 86696263HCID 86696263, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (53.1) (100 mg, 0.188 mmol) in THF (10 ml), TBAF (98 mg, 0.376 mmol) was added. The reaction mixture was stirred at rt for 3 h. The solvent was then removed under reduced pressure. The residue was dissolved in 30 ml of DCM, washed with water (10 ml×3) and brine (10 ml) successively. The organic phase was dried over Na2SO4, then filtered and concentrated. The residue was purified by silica gel chromatography (DCM/MeOH=10/1) to afford the title compound as pale yellow solid (22 mg, 28% yield). [Method 3]

Workup

  1. customThe solvent was then removed under reduced pressure
  2. dissolutionThe residue was dissolved in 30 ml of DCM
  3. washwashed with water (10 ml×3) and brine (10 ml) successively
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (DCM/MeOH=10/1)

Sources & evidence

ORD record
ord-794cf866334247ed8701c82eed824fed
Source dataset
uspto-grants-2015_06
Patent number
US09062045B2

Reaction notes

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