Tetrabutylammonium Fluoride → HCID 86758400, compound

HRID 2303359Notes

Reaction equation

HRID 2303359 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[CH:30]=1)[C:12](=[O:27])[CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][CH2:10][N:11]([CH2:28][C:29]1[CH:34]=[CH:33][N:32]=[C:31]([C:35]2[CH:40]=[C:39]([O:41][CH3:42])[C:38]([O:43][CH3:44])=[C:37]([O:45][CH3:46])[CH:36]=2)[CH:30]=1)[C:12](=[O:27])[CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86758401HCID 86758401, compound

Product 1

HCID 86758400HCID 86758400, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-[2-(tert-Butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]-Nα-(2-nitrobenzenesulfonyl)glycine amide (3.41 g) was dissolved in THF, and to the solution a THF solution (6.1 mL) of 1.0 M tetrabutylammonium fluoride was added, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate was added to the residue. The mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=10:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-3f47c61a43fe49a2abdc6d207f70f9ad
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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