Methyl iodide → HCID 21927859, compound

HRID 585542Notes

Reaction equation

HRID 585542 reaction equation
[NH2:1][C:2](=[O:11])[CH2:3][C:4]([CH3:10])([CH3:9])[CH2:5][C:6]([OH:8])=[O:7].[C:12](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[NH2:1][C:2](=[O:11])[CH2:3][C:4]([CH3:9])([CH3:10])[CH2:5][C:6]([O:8][CH3:12])=[O:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21927987HCID 21927987, compound

Product 1

HCID 21927859HCID 21927859, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-3,3-dimethyl-5-oxopentanoic acid (10.9 g; 68.6 mmoles) was dissolved in DMF (50 mL). Potassium carbonate (14.2 g; 103 mmoles) and methyl iodide (8.5 mL; 137.2 mmoles) were added and the reaction mixture was stirred overnight at room temperature. The reaction mixture was filtered, washing the filter cake with DMF. The DMF was removed under vacuum and the residue was suspended in ethyl acetate. The solids were removed by filtration and the ethyl acetate was removed under vacuum to give the product, methyl 5-amino-3,3-dimethyl-5-oxopentanoate, as a yellow oil (11.5 g; 97%). 1H NMR (400 MHz) DMSO-d6 δ 7.22 (1H, s, br), 6.73 (1H, s, br), 3.58 (3H, s), 2.39 (2H, s), 2.09 (2H, s), 1.02 (6H, s).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashing the filter cake with DMF
  3. customThe DMF was removed under vacuum
  4. customThe solids were removed by filtration
  5. customthe ethyl acetate was removed under vacuum

Sources & evidence

ORD record
ord-f3ee7ffe5fb946f5881bea59d0f05a7b
Source dataset
uspto-grants-2005_08
Patent number
US06933304B2

Reaction notes

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