Water → methyl 5-(4-bromo-2-formyl-N-isobutylanilino)pentanoate

HRID 1810773Notes

Reaction equation

HRID 1810773 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:7][CH:8]([CH3:10])[CH3:9])=[C:4]([CH:20]=[O:21])[CH:3]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([N:6]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:22])=[O:16])[CH2:7][CH:8]([CH3:10])[CH3:9])=[C:4]([CH:20]=[O:21])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 865955825-((4-Bromo-2-formylphenyl)(isobutyl)amino)pentanoic acid

Product 1

HCID 86595583methyl 5-(4-bromo-2-formyl-N-isobutylanilino)pentanoateYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 5-(4-bromo-2-formyl-N-isobutylanilino)pentanoic acid (15.0 g), potassium carbonate (7.0 g) in DMF (50 ml) was added dropwise a solution of iodomethane (8.4 g) in DMF (10 ml) at 0° C. under a nitrogen atmosphere. The mixture was warmed to room temperature, and stirred for 2 hours under a nitrogen atmosphere. After addition of water, the solution was extracted with ethyl acetate. The organic layer was washed with water and saturated saline, and dried over magnesium sulfate. After distilling off the solvent under reduced pressure, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to hexane:ethyl acetate=1:1) to obtain brown oil of methyl 5-(4-bromo-2-formyl-N-isobutylanilino)pentanoate (13.1 g). 1H-NMR (200 MHz, CDCl3) δ 0.86 (6H, d, J=6.6 Hz), 1.52-1.55 (4H, m), 1.75-1.90 (1H, m), 2.21-2.29 (2H, m), 2.95 (2H, d, J=7.2 Hz), 3.10-3.20 (2H, m), 3.64 (3H, s), 7.04 (1H, d, J=8.7), 7.54 (1H, dd, J=8, 7, 2.4 Hz), 7.89 (1H, d, J=2.4 Hz), 10.22 (1H, s).

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated saline
  3. dry with materialdried over magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1 to hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-c4da01232b2d49df9bce4a6c14c1f25b
Source dataset
uspto-grants-2013_01
Patent number
US08362058B2

Reaction notes

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