Potassium Carbonate → 5-(Benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid

HRID 12063

Reaction equation

HRID 12063 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].C([O:17][C:18](=[O:24])[CH2:19][CH2:20][CH2:21][CH2:22]Br)C.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:7]([N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:14])[CH2:22][CH2:21][CH2:20][CH2:19][C:18]([OH:24])=[O:17])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 80908N-Benzylglycine ethyl esterHCID 84580Ethyl 5-bromovalerate

Product 1

HCID 686801515-(Benzyl-ethoxycarbonylmethyl-amino)-pentanoic acidYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-benzylglycine ethyl ester (1.87 ml) and 5-bromovaleric acid ethyl ester (1.92 ml) are dissolved in dimethylformamide (100 ml) and stirred in the presence of potassium carbonate (1.66 g) for 2 days at room temperature. The reaction is quenched with saturated aqueous ammonium chloride solution, and extraction is carried out with ethyl acetate. After drying over sodium sulphate the combined organic phases are concentrated by evaporation. From the obtained residue, 5-(benzyl-ethoxycarbonylmethyl-amino)-pentanoic acid is isolated in a yield of 30% by chromatography using silica gel (ethyl acetate/heptane 1:5).

Workup

  1. customThe reaction is quenched with saturated aqueous ammonium chloride solution, and extraction
  2. dry with materialAfter drying over sodium sulphate the combined organic phases
  3. concentrationare concentrated by evaporation

Sources & evidence

ORD record
ord-d99e3ad127f8439ba0849a80a747879b
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Linked notes

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