Methyl iodide → HCID 178501239, compound

HRID 1019895Notes

Reaction equation

HRID 1019895 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]([O:11][C:12]([NH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]([C:21]([OH:23])=[O:22])[CH2:17][CH2:16]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].CI>CN(C)C=O>[CH3:1][O:22][C:21]([C@H:18]1[CH2:17][CH2:16][C@H:15]([NH:14][C:12]([O:11][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:13])[CH2:20][CH2:19]1)=[O:23]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178453972HCID 178453972, compound

Product 1

HCID 178501239HCID 178501239, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (877 mg, 6.34 mmol, 1.05 eq) is added at room temperature to a stirred solution of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1.50 g, 6.04 mmol, 1.0 eq) in N,N-dimethylformamide (30 mL), followed by methyl iodide (395 μL, 6.34 mmol, 1.05 eq). After 5 hours stirring at room temperature, solvent is evaporated and the residue is extracted with ethyl acetate (3×30 mL) and water (30 mL). The combined organic layers are washed with brine (30 mL), dried over sodium sulfate, filtered and concentrated to afford trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid methyl ester as a yellow solid (1.60 g, 98% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×30 mL) and water (30 mL)
  3. washThe combined organic layers are washed with brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8cc3232618974e01abfc585587cea5f2
Source dataset
uspto-grants-2014_05
Patent number
US08716280B2

Reaction notes

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