Iodoethane → HCID 178440102, compound

HRID 853130Notes

Reaction equation

HRID 853130 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]([C@H:16]1[CH2:21][CH2:20][C@H:19]([NH:22][S:23]([C:26]2[S:30][C:29]([CH3:31])=[N:28][C:27]=2[CH3:32])(=[O:25])=[O:24])[CH2:18][CH2:17]1)([O:8][Si](CC)(CC)CC)[C:4]([F:7])([F:6])[F:5].[Li][CH2:36][CH2:37]CC.[CH2:40](I)[CH3:41].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.CCCCCC>[CH2:36]([N:22]([C@H:19]1[CH2:18][CH2:17][C@H:16]([C:3]([OH:8])([C:2]([F:34])([F:1])[F:33])[C:4]([F:5])([F:6])[F:7])[CH2:21][CH2:20]1)[S:23]([C:26]1[S:30][C:29]([CH2:31][CH2:40][CH3:41])=[N:28][C:27]=1[CH3:32])(=[O:25])=[O:24])[CH3:37]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 2724141Tetrabutylammonium FluorideHCID 178418339ButyllithiumHCID 178477578HCID 178477578, compound

Product 1

HCID 178440102HCID 178440102, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 200 mg (0.36 mmol) of trans 2,4-dimethyl-thiazole-5-sulfonic acid [4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide in 5 mL of THF was cooled to −78° C. and treated dropwise with 0.25 mL of a 1.6 M solution of nBuLi in hexane. The solution was warmed to −30° C., treated with 1 mL (1.2 mmol) of ethyliodide, allowed to reach RT and then refluxed for 2 hrs. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave a residue that was redissolved in THF and treated with an excess of TBAF. Distribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation of the solvent and chromatography on silicagel with heptane/EtOAc 2:1 yielded 20 mg (11%) of trans 4-methyl-2-propyl-thiazole-5-sulfonic acid ethyl-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amide as a yellow oil, MS: 497 (M+H)+.

Workup

  1. customto reach RT
  2. temperaturerefluxed for 2 hrs
  3. dry with materialDistribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent
  4. customgave a residue that
  5. dry with materialDistribution between a saturated aqueous solution of NH4Cl and Et2O, drying of the combined organic phases over Na2SO4, evaporation of the solvent and chromatography on silicagel with heptane/EtOAc 2:1

Sources & evidence

ORD record
ord-6fd0b11d25dc478abb8ed0f28496e2a3
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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