Biphenyl-4-sulfonic acid [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(4-hydroxy-butyl)-amide → Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-(2-hydroxyethyl)-amide

HRID 2425125Notes

Reaction equation

HRID 2425125 reaction equation
C([Si](C1C=CC=CC=1)(C1C=CC=CC=1)[O:6][CH2:7][CH2:8][N:9]([CH2:25][CH2:26][CH2:27][CH2:28][OH:29])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11])(C)(C)C>[F-].C([NH3+])(C)(C)C>[OH:29][CH2:28][CH2:27][CH2:26][CH2:25][N:9]([CH2:8][CH2:7][OH:6])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=1)(=[O:12])=[O:11]

Participants

3

Reactant 1

HCID 59728311Biphenyl-4-sulfonic acid [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(4-hydroxy-butyl)-amide

Product 1

HCID 11624455Biphenyl-4-sulfonic acid-(4-hydroxybutyl)-(2-hydroxyethyl)-amide

Reagents, catalysts & solvents 1

HCID 21866379t-Butylammonium fluorideSolvent

Procedure

Biphenyl-4-sulfonic acid [2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-(4-hydroxy-butyl)-amide (1 g) was dissolved in tertiarybutylammonium fluoride (15 mL of 1 M in tetrahydrafuran) and stirring for 30 minutes. The solvent was evaporated and the residue dissolved in methylene chloride, washed with water and dried over Na2SO4. The product was purified by column chromatography (ethyl acetate: light petroleum) to give the title compound. δC (DMSO, 62.9 MHz): 25.1, 29.5, 48.9, 51.2, 57.9, 60.3, 127.1, 127.2, 127.6, 128.6, 129.2, 138.1, 138.4 and 144.1.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in methylene chloride
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customThe product was purified by column chromatography (ethyl acetate: light petroleum)

Sources & evidence

ORD record
ord-2d3df3ca72e440068f81e2ec50b61f5b
Source dataset
uspto-grants-2011_06
Patent number
US07964643B2

Reaction notes

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