Tetrabutylammonium Fluoride → HCID 86607937, compound

HRID 2104987Notes

Reaction equation

HRID 2104987 reaction equation
[Si]([O:8][C:9]1[C:10]([F:75])=[C:11]([CH:18]([C:45]2[N:46]([C:56]([C:69]3[CH:74]=[CH:73][CH:72]=[CH:71][CH:70]=3)([C:63]3[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=3)[C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)[CH:47]=[C:48]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)[N:49]=2)[NH:19][C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[C:26]([N:30]([C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:25][CH:24]=[CH:23]3)[CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCOC(C)=O>[C:34]([O:33][C:31]([N:30]([C:38]([O:40][C:41]([CH3:42])([CH3:44])[CH3:43])=[O:39])[C:26]1[C:27]2[C:22](=[CH:21][C:20]([NH:19][CH:18]([C:45]3[N:46]([C:56]([C:69]4[CH:70]=[CH:71][CH:72]=[CH:73][CH:74]=4)([C:63]4[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=4)[C:57]4[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=4)[CH:47]=[C:48]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[N:49]=3)[C:11]3[C:10]([F:75])=[C:9]([OH:8])[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[CH:12]=3)=[CH:29][CH:28]=2)[CH:23]=[CH:24][N:25]=1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86607938HCID 86607938, compound

Product 1

HCID 86607937HCID 86607937, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Intermediate 123.2 (635 mg, 0.619 mmol) in 5 mL THF, was added TBAF (1 M, 0.619 mL, 0.619 mmol). The mixture was stirred at rt for 30 min, then was diluted with EtOAc. The organic phase was washed with 0.1 N HCl, water (2×) and brine; dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes) to afford 509 mg (90%) of Intermediate 123.3 as a pale yellow solid.

Workup

  1. washThe organic phase was washed with 0.1 N HCl, water (2×) and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (0 to 75% EtOAc/hexanes)

Sources & evidence

ORD record
ord-3c55dd358b8c425ba2d81bdc10565fda
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

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