Methyl iodide → Methyl 2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoate

HRID 550949Notes

Reaction equation

HRID 550949 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH3:20][O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 2817530Boc-DL-Cha-OH

Product 1

HCID 4264602Methyl 2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoateYield 97.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-3-cyclohexyl-propionic acid (3.0 g, 11.1 mmol) and potassium carbonate (1.5 g, 11.1 mmol) in N,N-dimethylformamide (20 mL) was added methyl iodide (0.795 μL; 12.1 mmol). The reaction mixture was stirred at room temperature overnight. To the reaction mixture was added ethyl acetate (100 mL) and the solution was washed with water (3×100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give the title intermediate as an oil (3.1 g) which was used directly in the next step.

Workup

  1. washthe solution was washed with water (3×100 mL)
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-694537b3b173448da91196b457c89724
Source dataset
uspto-grants-2011_05
Patent number
US07947710B2

Reaction notes

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