Tetrabutylammonium Fluoride → 4-[((2S)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-hydroxypropyl)oxy]phenol

HRID 990076Notes

Reaction equation

HRID 990076 reaction equation
[Si]([O:18][C:19]1[CH:51]=[CH:50][C:22]([O:23][CH2:24][C@@H:25]([OH:49])[CH2:26][NH:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH2:39][C:40]3[N:44]=[C:43]([C:45]([CH3:48])([CH3:47])[CH3:46])[O:42][N:41]=3)(=[O:38])=[O:37])=[CH:32][CH:31]=2)=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.[Cl-].[NH4+]>[C:45]([C:43]1[O:42][N:41]=[C:40]([CH2:39][S:36]([C:33]2[CH:34]=[CH:35][C:30]([CH2:29][CH2:28][NH:27][CH2:26][C@H:25]([OH:49])[CH2:24][O:23][C:22]3[CH:21]=[CH:20][C:19]([OH:18])=[CH:51][CH:50]=3)=[CH:31][CH:32]=2)(=[O:37])=[O:38])[N:44]=1)([CH3:48])([CH3:46])[CH3:47]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 11456872(2S)-1-(4-{[tert-butyl(diphenyl)silyl]oxy}phenoxy)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-propanol

Product 1

HCID 114659764-[((2S)-3-{[4-({[5-(tert-butyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-2-hydroxypropyl)oxy]phenolYield 63.5%

Reagents, catalysts & solvents 2

HCID 25517Ammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the amino alcohol of Example 14(0.650 g, 0.90 mmol) in THF (12 mL) was added a 1 M solution of TBAF (0.225 mL, 0.225 mmol). The reaction mixture was stirred for 6 h. TLC showed the absence of starting material, therefore 5 drops of a saturated aqueous ammonium chloride solution was added. The reaction mixture was evaporated in vacuo to dryness and the residue was flash chromatographed (silica gel; dichloromethane/chloroform/methanol: 15/5/3) to afford 0.280 g of the title compound as a white foam.

Workup

  1. customThe reaction mixture was evaporated in vacuo to dryness
  2. customchromatographed (silica gel; dichloromethane/chloroform/methanol: 15/5/3)

Sources & evidence

ORD record
ord-5932930e01fb4ab584a4ac2b75441f53
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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