Triethylamine → 2-[1-(4-benzyloxyphenyl)-2-(4-fluorophenyl)-2-oxoethyl]-4-methyl-3-oxo-N-phenylpentanamide

HRID 277568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277568
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]([C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[C:17]([NH2:19])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1.C(N([CH2:39][CH3:40])CC)C>[Br-].C([N+]1C(C)=C(CCO)SC=1)C.CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH:16]([C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])[C:17]([NH:19][C:40]2[CH:39]=[CH:4][CH:3]=[CH:2][CH:1]=2)=[O:18])[C:30]([C:29]2[CH:32]=[CH:33][C:26]([F:25])=[CH:27][CH:28]=2)=[O:31])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 680234-FluorobenzaldehydeHCID 540483912-(4-Benzyloxyphenylmethylene)-4-methyl-3-oxopentanamide

Produkt 1

HCID 183146162-[1-(4-benzyloxyphenyl)-2-(4-fluorophenyl)-2-oxoethyl]-4-methyl-3-oxo-N-phenylpentanamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

Step B—A solution of 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (2 mmol), 2-(4-benzyloxyphenylmethylene)-4-methyl-3-oxopentanamide (8 mmol), 4-fluorobenzaldehyde (8 mmol) and triethylamine (1 mL) in EtOH (100 mL) is heated at reflux. The progress of the reaction is monitored by tlc. When the reaction is complete, the solvent is removed under reduced pressure and the residue is dissolved in EtOAc. The solution is washed with dilute HCl, then dried and evaporated. The residue is chromatographed to afford 2-[1-(4-benzyloxyphenyl)-2-(4-fluorophenyl)-2-oxoethyl]-4-methyl-3-oxo-N-phenylpentanamide, 14 (R=4-benzyloxy).

Aufarbeitung

  1. temperatureat reflux
  2. customthe solvent is removed under reduced pressure
  3. dissolutionthe residue is dissolved in EtOAc
  4. washThe solution is washed with dilute HCl
  5. customdried
  6. customevaporated
  7. customThe residue is chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-841f15a85bff417791821e0456f47c9f
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355810B1

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