Methyl iodide → HCID 178501130, compound

HRID 2118256Notes

Reaction equation

HRID 2118256 reaction equation
[Na].[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8][CH2:7]1)=[O:5].[CH3:27]I>CO.CN(C=O)C>[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][N:13]([CH3:27])[S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH2:8][CH2:7]1)=[O:5]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 178501133HCID 178501133, compound

Product 1

HCID 178501130HCID 178501130, compoundYield 97.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

100 mg (4 mmol, 1.1 eq) of sodium were reacted in 2 mL of MeOH. Then 1.33 g (3.5 mmol) of trans-4-[(4-trifluoromethyl-benzenesulfonylamino)-methyl]-cyclohexane carboxylic acid methyl ester dissolved in 3 mL of dry DMF were added, followed by 0.44 mL (7 mmol, 2 eq) of CH3I. The mixture was stirred at RT for 2 h, then poured into ice-water and extracted with 3 portions of 15 mL of CH2Cl2. The combined organic phases were washed with H2O and brine, dried over anhydrous Na2SO4 and evaporated, leaving 1.34 g (97%) of trans-4-{[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-methyl}-cyclohexane-carboxylic acid methyl ester as white solid, MS: 411 (M+NH4+).

Workup

  1. additionwere added
  2. extractionextracted with 3 portions of 15 mL of CH2Cl2
  3. washThe combined organic phases were washed with H2O and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-445821c56e8b4507999ab9f59a08ee36
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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