Acetonitrile → Ethyl 3-(dibenzylamino)propanoate

Reaktionsgleichung

C(=O)([O-])[O-].[Na+].[Na+].Cl.[CH2:8]([O:10][C:11](=[O:15])[C@H:12]([CH3:14])N)[CH3:9].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24](#[N:26])[CH3:25]>>[CH2:16]([N:26]([CH2:24][C:25]1[CH:21]=[CH:22][CH:17]=[CH:18][CH:19]=1)[CH2:14][CH2:12][C:11]([O:10][CH2:8][CH3:9])=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

Edukt 4

HCID 6342Acetonitrile

HCID 7498Benzyl Bromide

HCID 10340Sodium Carbonate

HCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Produkt 1

HCID 44791227Ethyl 3-(dibenzylamino)propanoate

Versuchsvorschrift

Sodium carbonate (21.1 g, 199 mmol) was added to a suspension of fl-alanine ethyl ester hydrochloride (10.2 g, 66.4 mmol) and benzyl bromide (16.2 mL, 136 mmol) in acetonitrile (265 mL). The reaction mixture was stirred at ambient temperature overnight and then filtered through a layer of CELITE filter aid. The filter cake was rinsed with acetonitrile (100 mL). The filtrate was concentrated under reduced pressure to provide 20.28 g of ethyl 3-dibenzylaminopropionate as a pale yellow oil.

Aufarbeitung

filtrationfiltered through a layer of CELITE
filtrationfilter aid
washThe filter cake was rinsed with acetonitrile (100 mL)
concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag: ord-d674fba9e1e44c9fab3bae00d59fca65
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541438B2

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