Potassium Carbonate → Ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoate

HRID 2299105

Reaction equation

HRID 2299105 reaction equation
[CH2:1]([NH:8][CH:9]([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:18][C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:9]([CH3:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 236384Ethyl 3-(benzylamino)butanoate

Product 1

HCID 18379207Ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoateYield 82.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of ethyl 3-(benzylamino)butanoate (5.9 g, 26.7 mmol), methyl bromoacetate (3.0 ml, 31.7 mmol) and potassium carbonate (7.4 g, 53.5 mmol) in acetonitrile (100 ml), was stirred at room temperature for 18 hs. The reaction was filtered through celite and concentrated to give ethyl 3-[benzyl(2-methoxy-2-oxoethyl)amino]butanoate (6.45 g, 82%) as a clear oil, MS (M+H)+=294.

Workup

  1. filtrationThe reaction was filtered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1172e6df8a92440db103cfa3ddf1bc7d
Source dataset
uspto-grants-2002_12
Patent number
US06495565B2

Linked notes

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