Ethyl bromoacetate → (s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl ester

HRID 29061

Reaktionsgleichung

Reaktionsgleichung von HRID 29061
[CH2:1]([NH:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[CH2:2][CH:3]=[CH2:4].C([O-])([O-])=O.[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21]>CN(C=O)C.CCOCC>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][N:5]([CH2:1][CH2:2][CH:3]=[CH2:4])[C@H:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[CH3:21]

Komponenten

6

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10559173But-3-enyl-((S)-1-phenyl-ethyl)-amine

Produkt 1

HCID 10956339(s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl esterAusbeute 94,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of But-3-enyl-((S)-1-phenyl-ethyl)-amine (6.37 g, 36.4 mmol) in 150 mL of DMF at 0° C. is added K2CO3 (10.0 g, 72.8 mmol) in small portions. After stirring at 0° C. for 10 min, ethylbromoacetate (8.35 g, 54.6 mmol) izs added slowly. The reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs. The solution is diluted with 200 mL of ether, and washed with 3×100 ml of water. The crude product is purified by chromatography (hexane/CH2Cl2: 50/50) to give a pale liquid(8.5 g, 94.5%). (NMR and MS data confirmed, U-4117-58).

Aufarbeitung

  1. stirringThe reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs
  2. washwashed with 3×100 ml of water
  3. customThe crude product is purified by chromatography (hexane/CH2Cl2: 50/50)

Quellen und Nachweise

ORD-Eintrag
ord-ba3faff163924c36bd90fcaa1113892f
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07419975B2

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