Ethyl Acetate → HCID 12070457, compound

HRID 983662Notes

Reaction equation

HRID 983662 reaction equation
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([N:6]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[CH3:7])=[C:4]([CH:17]=[O:18])[CH:3]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI.CN(C=O)C.C(OCC)(=O)C>CN(C=O)C.O>[CH3:19][O:13][C:12](=[O:14])[CH2:11][CH2:10][CH2:9][CH2:8][N:6]([CH3:7])[C:5]1[CH:15]=[CH:16][C:2]([Br:1])=[CH:3][C:4]=1[CH:17]=[O:18]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12070446HCID 12070446, compoundHCID 86587335iodomethane DMF

Product 1

HCID 12070457HCID 12070457, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(4-bromo-2-formyl-N-methylanilino)pentanoic acid (3.0 g) in DMF(8 ml), potassium carbonate (1.6 g) and a solution of methyl iodide/DMF (1.6 g/2 ml) were added at room temperature, and the resulting mixture was stirred for 2 hours. Ethyl acetate and water were added to the mixture, and the organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated to give yellow oil of 5-(4-bromo-2-formyl -N-methylanilino)pentanoic acid methylester (3.0 g, yield 97%). 1H-NMR(CDCl3, δ, 300 MHz): 1.58-1.64(4H, m), 2.28(2H, t, J=6.8 Hz), 2.83(3H, s), 3.09(2H, t, J=6.8 Hz), 3.63(3H, s), 6.95(1H, d, J=8.8 Hz), 7.51(1H, dd, J=8.8, 2.4 Hz), 7,83(1H, d, J=2.4 Hz), 10.14(1H, s). FAB-MS ([M+Na]+): 350. IR(neat, cm−1): 1735, 1681.

Workup

  1. customthe organic layer was separated
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a767ca0b01f24c5da278363e781b9358
Source dataset
uspto-grants-2005_03
Patent number
US06864367B2

Reaction notes

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