Tetrabutylammonium Fluoride → HCID 69201859, compound

HRID 2220650Notes

Reaction equation

HRID 2220650 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:39][Si](CC)(CC)CC)[CH2:16][NH:17][C@H:18]([CH3:38])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:11][C:10]=1[NH:47][S:48]([CH3:51])(=[O:50])=[O:49])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:39])[CH2:16][NH:17][C@H:18]([CH3:38])[CH2:19][O:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][C:30]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:29][CH:28]=3)=[CH:23][CH:22]=2)=[CH:11][C:10]=1[NH:47][S:48]([CH3:51])(=[O:49])=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 69201025HCID 69201025, compound

Product 1

HCID 69201859HCID 69201859, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethyl 4′-{(R)-2-[(R)-2-(4-benzyloxy-3-methanesulfonylaminophenyl)-2-triethylsilanyloxyethylamino]propyloxy}biphenyl-4-carboxylate was dissolved in tetrahydrofuran (5.70 mL), and a 1 mol/L solution of tetrabutylammonium fluoride in tetrahydrofuran (0.63 mL) was added dropwise to the solution at room temperature with stirring. After being stirred at that temperature for 13 hrs, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel flash column chromatography (eluent: methylene chloride/ethyl acetate=1/1 and methylene chloride/methanol=10/1) to afford the title compound (0.284 g).

Workup

  1. stirringAfter being stirred at that temperature for 13 hrs
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by silica gel flash column chromatography (eluent: methylene chloride/ethyl acetate=1/1 and methylene chloride/methanol=10/1)

Sources & evidence

ORD record
ord-b7f0128d81cf44ba94afb07339a804bb
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

Loading…