Tetrabutylammonium Fluoride → N-{4'-Fluoro-2'-[(R)-1-hydroxyethyl]-1,1'-biphenyl-2-yl}-4-methoxybenzenesulfonamide

HRID 2224621Notes

Reaction equation

HRID 2224621 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14](COCC[Si](C)(C)C)[S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])=[C:4]([C@H:34]([OH:36])[CH3:35])[CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[NH:14][S:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)(=[O:16])=[O:17])=[C:4]([C@H:34]([OH:36])[CH3:35])[CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69254268N-{4'-Fluoro-2'-[(R)-1-hydroxyethyl]-1,1'-biphenyl-2-yl}-4-methoxy-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide

Product 1

HCID 69253499N-{4'-Fluoro-2'-[(R)-1-hydroxyethyl]-1,1'-biphenyl-2-yl}-4-methoxybenzenesulfonamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-{4′-Fluoro-2′-[(R)-1-hydroxyethyl]-1,1′-biphenyl-2-yl }-4-methoxy-N-{[2-(trimethylsilyl)ethoxy]methyl}benzenesulfonamide (0.28 g, 0.51 mmol) was dissolved in tetrahydrofuran (10 mL) and tetrabutylammonium fluoride in tetrahydrofuran (1.0 M, 0.76 mL, 0.76 mmol) was added. The solution was heated at reflux for six hours. The solution was concentrated in vacuo and the mixture was dissolved in ethyl acetate and washed with water. The solution was dried over anhydrous magnesium sulfate and the solvent was removed in vacuo. The product was passed through a silica gel plug (5:1 hexane: ethyl acetate followed by 1:1 hexane:ethyl acetate) to yield the title compound as a solid (0.135 g, 66% ), m.p. 137-138° C. The NM spectrum of the title compound was consistent with rotamers. The peaks attributed to individual rotamers in the 1H NMR spectrum coalesced at 90° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for six hours
  3. concentrationThe solution was concentrated in vacuo
  4. dissolutionthe mixture was dissolved in ethyl acetate
  5. washwashed with water
  6. dry with materialThe solution was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8bd3ed02c7c04cb799ad8a5cb7cceef3
Source dataset
uspto-grants-2008_05
Patent number
US07378427B2

Reaction notes

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