Tetrabutylammonium Fluoride → HCID 86760475, compound

HRID 1268940Notes

Reaction equation

HRID 1268940 reaction equation
[C:1]([C:5]1[CH:47]=[CH:46][C:8]([O:9][C@@H:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][N:31]=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=4)=[CH:36][CH:35]=3)[CH3:33])=[CH:23][CH:22]=2)[C:11]([O:13]CC[Si](C)(C)C)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C@@H:10]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][O:30][N:31]=[C:32]([C:34]3[CH:35]=[CH:36][C:37]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=4)=[CH:38][CH:39]=3)[CH3:33])=[CH:23][CH:22]=2)[C:11]([OH:13])=[O:12])=[CH:46][CH:47]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86760476HCID 86760476, compound

Product 1

HCID 86760475HCID 86760475, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out according to Reference example 7 using 2-trimethylsilylethyl (S)-2-(4-t-butylphenoxy)-3-[4-[2-[[1-[4-(2-pyridyl)phenyl]ethylidene]aminoxy]ethoxy]phenyl]propionate (310 mg) obtained from Reference example 12 and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.7 ml). The resulting residue was purified by chromatography on a silica gel column (eluant; methylene chloride/methanol=24/1˜19/1), and then the obtained compound was filtered off and washed with isopropyl ether and hexane to afford the target compound (180 mg) as colorless crystals.

Workup

  1. customobtained from Reference example 12
  2. customThe resulting residue was purified by chromatography on a silica gel column (eluant; methylene chloride/methanol=24/1˜19/1)
  3. filtrationthe obtained compound was filtered off
  4. washwashed with isopropyl ether and hexane

Sources & evidence

ORD record
ord-cb58994953354fcc86146ccc24e0f4b1
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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