Tetrabutylammonium Fluoride → HCID 22711104, compound

HRID 352885Notes

Reaction equation

HRID 352885 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[S:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH:25]([CH2:36][CH2:37][O:38][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH2:24]2)(=[O:22])=[O:21])(=O)=O)C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:32]([O:31][C:29]([N:26]1[CH2:27][CH2:28][N:23]([S:20]([C:11]2[NH:10][C:18]3[C:13]([CH:12]=2)=[CH:14][C:15]([Cl:19])=[CH:16][CH:17]=3)(=[O:22])=[O:21])[CH2:24][CH:25]1[CH2:36][CH2:37][OH:38])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 22709507HCID 22709507, compound

Product 1

HCID 22711104HCID 22711104, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-[(1-benzenesulfonyl-5-chloroindol-2-yl)sulfonyl]-1-(tert-butoxycarbonyl)-2-[2-(tert-butyldiphenylsilyloxy)ethyl]piperazine (4.48 g) in tetrahydrofuran (20 ml) was added a 1.OM tetrahydrofuran solution (5.5 ml) of tetrabutylammonium fluoride, followed by stirring at room temperature for 3.5 hours. After concentration under reduced pressure, the residue was purified by flash column chromatography (ethyl acetate:hexane=1:9 to 1:0) using as a carrier silica gel, whereby the title compound (0.75 g) was obtained as a colorless solid.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe residue was purified by flash column chromatography (ethyl acetate:hexane=1:9 to 1:0)
  3. customwas obtained as a colorless solid

Sources & evidence

ORD record
ord-46c4b660ca684fc5b0a18b5cf1b3b49e
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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