Bromochloromethane → (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone

HRID 2301732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2301732
C[O:2][C:3](=O)[C@H:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[N:5]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Br[CH2:28][Cl:29].CCCCCC.C([Li])CCC.[Cl-].[NH4+]>O1CCCC1>[Cl:29][CH2:28][C:3](=[O:2])[C@@H:4]([N:5]=[C:6]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 6333BromochloromethaneHCID 25517Ammonium ChlorideHCID 11142452Rac-methyl-n-(diphenylmethylene)phenylalaninateHCID 178418244HCID 178418244, Verbindung

Produkt 1

HCID 11325911(3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanoneAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

N-(diphenylmethylene)-L-phenylalanine methyl ester (3.35 g) and bromochloromethane (0.83 ml) were added to dehydrated tetrahydrofuran (97 ml), and the mixture was cooled to −78° C. Then, a 1.53 M n-butyllithium hexane solution (8.3 ml) was added thereto. The mixture was stirred for 35 minutes. A saturated aqueous solution of ammonium chloride was added to the reaction solution to terminate the reaction. The resulting reaction solution was extracted twice with ethyl acetate at room temperature. The ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. After magnesium sulfate was removed, the ethyl acetate solution was concentrated to obtain desired (3S)-1-chloro-3-(diphenylmethylene)amino-4-phenyl-2-butanone (3.52 g) in a yield of 99.7%.

Aufarbeitung

  1. customto terminate
  2. customthe reaction
  3. customThe resulting reaction solution
  4. extractionwas extracted twice with ethyl acetate at room temperature
  5. washThe ethyl acetate layer was then washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customAfter magnesium sulfate was removed
  8. concentrationthe ethyl acetate solution was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-9bf1ede13b524587936e6da71719234e
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06500985B2

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