Tetrabutylammonium Fluoride → HCID 69206630, compound

HRID 748651Notes

Reaction equation

HRID 748651 reaction equation
[CH3:1][N:2]([CH3:25])[S:3]([N:6]1[CH:10]=[C:9]([CH:11]([OH:17])[C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[C:7]1[Si](C(C)(C)C)(C)C)(=[O:5])=[O:4].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][N:2]([CH3:25])[S:3]([N:6]1[CH:10]=[C:9]([CH:11]([OH:17])[C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59751486HCID 59751486, compound

Product 1

HCID 69206630HCID 69206630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(tert-butyl-dimethyl-silanyl)-4-(hydroxy-thiophen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-E1) (2.5 g, 6.2 mmol) in THF (60 mL) was treated with tetrabutylammonium fluoride (TBAF) (6.9 mL of a 1M soln) at 0° C. for 1 h and at rt for 3 h. The reaction mixture was subjected to an aqueous work-up and the product was purified by chromatography on silica gel with EtOAc to give 4-(hydroxy-thiophen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide as a white solid, 1.43 g. 4-(Hydroxy-thiophen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (0.5 g, 1.74 mmol) in dichloromethane (25 mL) was reacted with trifluoroacetic acid (4.3 mL, 56 mmol) and triethylsilane (TES) (2.2 mL, 14 mmol) at rt for 18 h. The mixture was quenched with water and solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 50% EtOAc: hexane to yield 4-thiophen-2-ylmethyl-imidazole-1-sulfonic acid dimethylamide (Intermediate-E2) 0.44 g.

Workup

  1. customthe product was purified by chromatography on silica gel with EtOAc

Sources & evidence

ORD record
ord-92467fe03f6b4dcc8d9e593a6154ea8c
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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