Tetrabutylammonium Fluoride → HCID 23157439, compound

HRID 508061Notes

Reaction equation

HRID 508061 reaction equation
[Si]([O:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][N:23]([S:38]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=3[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[C:24]3[CH:29]=[CH:28][C:27]([CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])=[C:26]([F:37])[CH:25]=3)[CH:17]=2)=[C:11]([CH3:50])[CH:10]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:37][C:26]1[CH:25]=[C:24]([N:23]([CH2:22][C:18]2[CH:17]=[C:16]([C:12]3[C:13]([CH3:15])=[CH:14][C:9]([OH:8])=[CH:10][C:11]=3[CH3:50])[CH:21]=[CH:20][CH:19]=2)[S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:39])=[O:40])[CH:29]=[CH:28][C:27]=1[CH2:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59434116HCID 59434116, compound

Product 1

HCID 23157439HCID 23157439, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(4-{[(4′-{[tert-butyl(dimethyl)silyl]oxy}-2′,6′-dimethylbiphenyl-3-yl)methyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate (6.32 g, 8.76 mmol) in tetrahydrofuran (60 mL) was added tetrabutylammonium fluoride (1 M solution, 9.64 mL, 9.64 mmol) under stirring at room temperature, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1) to give the title compound (4.0 g, yield 75%) as colorless crystals.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-590223e0d89843c18c62bf8b58b27c01
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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