Tetrabutylammonium Fluoride → HCID 86591438, compound

HRID 1268939Notes

Reaction equation

HRID 1268939 reaction equation
[C:1]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:6]=[CH:5][C:4]([C:7](=[N:9][O:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:31][C:32]3[CH:37]=[CH:36][C:35]([C:38]([CH3:41])([CH3:40])[CH3:39])=[CH:34][CH:33]=3)[C:22]([O:24]CC[Si](C)(C)C)=[O:23])=[CH:16][CH:15]=2)[CH3:8])=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:1]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH:2]=[CH:3][C:4]([C:7](=[N:9][O:10][CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C@H:21]([O:31][C:32]3[CH:33]=[CH:34][C:35]([C:38]([CH3:39])([CH3:40])[CH3:41])=[CH:36][CH:37]=3)[C:22]([OH:24])=[O:23])=[CH:16][CH:15]=2)[CH3:8])=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86591439HCID 86591439, compound

Product 1

HCID 86591438HCID 86591438, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The reaction was carried out according to Reference example 7 using 2-trimethylsilylethyl (S)-3-[4-[2-[[1-(4-biphenylyl)ethylidene]aminoxy]ethoxy]phenyl]-2-(4-t-butylphenoxy)propionate (300 mg) obtained from Reference example 10 and a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.20 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 (170 mg) as colorless crystals.

Workup

  1. customobtained from Reference example 10
  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-e4d72a040e0345c789e3d6cd5d3c2288
Source dataset
uspto-grants-2007_04
Patent number
US07199139B2

Reaction notes

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