Tetrabutylammonium Fluoride → 2-Methylpentane

HRID 1255352Notes

Reaction equation

HRID 1255352 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:19]([N:23]([CH2:59][CH2:60][CH2:61][O:62][Si](C(C)(C)C)(C)C)[C:24](=[O:58])[CH2:25][CH2:26][O:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][N:37]2[CH2:56][CH2:55][C:40]3([O:45][CH2:44][CH2:43][N:42]([C:46]([C:48]4[N:49]=[C:50]([CH2:53][CH3:54])[S:51][CH:52]=4)=[O:47])[CH2:41]3)[CH2:39][CH2:38]2)[C:31]=1[Cl:57])[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH3:33][CH2:32][CH2:31][CH:30]([CH3:35])[CH3:29].[CH2:19]([N:23]([CH2:59][CH2:60][CH2:61][OH:62])[C:24](=[O:58])[CH2:25][CH2:26][O:27][CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([CH2:36][N:37]2[CH2:38][CH2:39][C:40]3([O:45][CH2:44][CH2:43][N:42]([C:46]([C:48]4[N:49]=[C:50]([CH2:53][CH3:54])[S:51][CH:52]=4)=[O:47])[CH2:41]3)[CH2:55][CH2:56]2)[C:31]=1[Cl:57])[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 58168573HCID 58168573, compound

Product 2

HCID 78922-MethylpentaneHCID 58168504HCID 58168504, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (1M in THF, 0.62 mL) was added to a solution of N-butyl-N-(3-(tert-butyldimethylsilyloxy)propyl)-3-(2-chloro-3-((4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamide [Example 80, step a] (0.47 g) in THF (10 mL) and the mixture stirred overnight. The solvent was evaporated and the residue purified by flash silica chromatography, elution gradient 1:1:0.05 ethyl acetate:isohexane:triethylamine to 95:5 ethyl acetate:triethylamine, to give the subtitled compound as a clear oil. Yield 0.40 g.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by flash silica chromatography, elution gradient 1:1:0.05 ethyl acetate

Sources & evidence

ORD record
ord-c4917435ed2c492fa84fcc4d0dc56d86
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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