Methyl iodide → HCID 178468184, compound

HRID 2118261Notes

Reaction equation

HRID 2118261 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[CH3:31][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>C1COCC1>[C:1]([O:5][C:6](=[O:30])[CH:7]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([N:15]([CH3:29])[S:16]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:11][CH2:10]1)[CH3:31])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 178484859HCID 178484859, compound

Product 1

HCID 178468184HCID 178468184, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 1.19 g (2.6 mmol) trans-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-acetic acid tert-butyl ester in 20 ml of anhydrous THF was cooled to −78° and treated dropwise with a 1M solution of lithium bis-(trimethylsilyl)-amide in THF (6.2 ml, 2.5 eq). The mixture was allowed to reach RT within ca. 1 h and cooled again to −78°. A solution of 0.18 ml (2.9 mmol, 1.1 eq) of iodomethane in 2.5 ml of THF was added and the mixture allowed reach RT within ca. 1 h. After addition of ice, the mixture was extracted with EtOAc, dried over Na2SO4, and the solvent evaporated. Column chromatography on silica gel gave 600 mg (49%) of trans-2-{4-[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-cyclohexyloxy}-propionic acid tert-butyl ester as a colorless solid, MS: 483 (M+NH4+).

Workup

  1. temperaturecooled again to −78°
  2. waitthe mixture allowed reach RT within ca. 1 h
  3. additionAfter addition of ice
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. customthe solvent evaporated

Sources & evidence

ORD record
ord-3b9acf65bee94226981f5ada7348397d
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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