Tetrabutylammonium Fluoride → HCID 178464521, compound

HRID 853129Notes

Reaction equation

HRID 853129 reaction equation
[CH2:1]([N:3]([C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20]([O:29][Si](CC)(CC)CC)([C:25]([F:28])([F:27])[F:26])[C:21]([F:24])([F:23])[F:22])[CH2:16][CH2:15]1)[S:4]([C:7]1[N:8]=[C:9]([CH3:13])[N:10]([CH3:12])[CH:11]=1)(=[O:6])=[O:5])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH2:1]([N:3]([C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20]([OH:29])([C:25]([F:28])([F:26])[F:27])[C:21]([F:23])([F:24])[F:22])[CH2:18][CH2:19]1)[S:4]([C:7]1[N:8]=[C:9]([CH3:13])[N:10]([CH3:12])[CH:11]=1)(=[O:6])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 178464527HCID 178464527, compound

Product 1

HCID 178464521HCID 178464521, compoundYield 40.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 130 mg (0.23 mmol) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide in 2 mL of THF was treated with an excess of TBAF and stirred for 2 hrs at RT. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases, evaporation of the solvent and column chromatography on silica gel with EtOAc/heptane 1:1 gave 42 mg (25%) of trans 1,2-dimethyl-1H-imidazole-4-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a yellow viscous oil, MS: 452 (M+H)+.

Workup

  1. dry with materialDistribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases, evaporation of the solvent and column chromatography on silica gel with EtOAc/heptane 1:1

Sources & evidence

ORD record
ord-631d4e81efe44ec09d87d4758d9e4adf
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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