Benzyl Bromide → HCID 44223288, Verbindung

HRID 722799

Reaktionsgleichung

Reaktionsgleichung von HRID 722799
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][CH3:5].[CH:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:15]([N:1]([C@@H:2]([CH2:3][CH2:4][CH3:5])[C:6]([O:8][CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)=[O:7])[CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1

Komponenten

5

Edukt 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 65098L-Norvaline

Produkt 1

HCID 44223288HCID 44223288, VerbindungAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of L-norvaline (685 mg, 5.85 mmol) in MeCN (15 mL), BnBr (3.48 mL, 29.24 mmol) and K2CO3 (4.04 g, 29.24 mmol) were added. The mixture was stirred at 60° C. for 9 h, and then cooled down to room temperature and filtered, washing the solid with EtOAc. The filtrates were concentrated in vacuo and the residue purified by column chromatography on silica (100% hexane to hexane/EtOAc 5:1) to obtain benzyl ester 9 as a colorless oil (1.6 g, 71% yield).

Aufarbeitung

  1. temperaturecooled down to room temperature
  2. filtrationfiltered
  3. washwashing the solid with EtOAc
  4. concentrationThe filtrates were concentrated in vacuo
  5. customthe residue purified by column chromatography on silica (100% hexane to hexane/EtOAc 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-eaeff5e461914e19836b8db465d0611d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138547B2

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