Trifluoroacetic acid → HCID 59751490, compound

HRID 748652Notes

Reaction equation

HRID 748652 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[C:9]([CH:11](O)[C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4].FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[CH3:18][N:2]([CH3:1])[S:3]([N:6]1[CH:10]=[C:9]([CH2:11][C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69206630HCID 69206630, compound

Product 1

HCID 59751490HCID 59751490, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 mixture was quenched with water and solid NaHCO3
  2. customthe residue was purified by chromatography on silica gel with 50% EtOAc

Sources & evidence

ORD record
ord-58c6b21f397f4b50825159fc21b8d943
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Reaction notes

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