Triethylamine → HCID 18447315, compound

HRID 1269903Notes

Reaction equation

C(N(CC)CC)C.Br[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].[CH2:18]([O:20][C:21](=[O:31])[CH2:22][NH:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH3:19]>C(#N)C>[CH2:24]([N:23]([CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:31])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Under a nitrogen atmosphere, triethylamine (1.73 ml, 0.01243 mol) and ethyl 5-bromovalerate (1.72 ml, 0.0109 mol) were added to a solution of N-benzylglycine ethyl ester (2.0 g, 0.0103 mol) in acetonitrile (40 ml) at room temperature, and the resulting mixture was heated at 60° C. After 1 hour, the mixture was refluxed. After 9 hours, the mixture was concentrated under reduced pressure, and the resulting residue was extracted with water (200 ml) and ethyl acetate (200 ml×2) and the organic layer was dried over anhydrous magnesium sulfate. The organic layer dried was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate) to obtain ethyl 5-[benzyl(2-ethoxy-2-oxoethyl)amino]pentanoate (1.2473 g, 37%).

Workup

temperaturethe mixture was refluxed
waitAfter 9 hours
concentrationthe mixture was concentrated under reduced pressure
extractionthe resulting residue was extracted with water (200 ml) and ethyl acetate (200 ml×2)
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customThe organic layer dried
concentrationwas concentrated under reduced pressure
customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record: ord-2cd13afa9d724b599b14fa8e07ee5020
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199147B2

Reaction notes

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