Tetrabutylammonium Fluoride → HCID 68771290, compound

HRID 747283Notes

Reaction equation

HRID 747283 reaction equation
[CH3:1][N:2]([CH3:30])[S:3]([N:6]1[CH:10]=[C:9]([CH:11]([OH:22])[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=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]([CH3:30])[S:3]([N:6]1[CH:10]=[C:9]([CH:11]([OH:22])[C:12]2[CH:21]=[CH:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=2)[N:8]=[CH:7]1)(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 59749557HCID 59749557, compound

Product 1

HCID 68771290HCID 68771290, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(tert-Butyl-dimethyl-silanyl)-4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (Intermediate-I1) (2.6 g, 5.4 mmol) in THF (30 mL) was treated with tetrabutylammonium fluoride (TBAF) (5.8 mL of a 1M soln) at rt for 1 h. The reaction mixture was subjected to an aqueous work-up and the product was purified by chromatography on silica gel with 66% EtOAc:hexane to give 4-(hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide as a white solid, 1.54 g (80%). 4-(Hydroxy-naphthalen-2-yl-methyl)-imidazole-1-sulfonic acid dimethylamide (1.0 g, 3.0 mmol) was deoxygenated with TES in TFA according to the applicable procedures outlined in Method A to give 4-naphthalen-2-yl-methyl-imidazole-1-sulfonic acid dimethylamide (Intermediate-I2) as a white solid 0.55 g, (58%).

Workup

  1. customthe product was purified by chromatography on silica gel with 66% EtOAc

Sources & evidence

ORD record
ord-6fa800669e8842298b6263ad3bb0733c
Source dataset
uspto-grants-2008_07
Patent number
US07396849B2

Reaction notes

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