Phenylalanine amide → Tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

HRID 227253

Reaktionsgleichung

Reaktionsgleichung von HRID 227253
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:15][C@H:16]([C:24]([NH2:26])=[O:25])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCO>[CH2:17]([CH:16]1[NH:15][C:11]2([CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[NH:26][C:24]1=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 445694Phenylalanine amideHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylate

Produkt 1

HCID 68839899Tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

N-tert-Butyloxycarbonylpiperidone (6.0 g, 29.8 mmol) was added to a solution of phenylalaninamide (4.9 g, 29.8 mmol) in dry EtOH (20 ml) and the mixture was heated under reflux for 2.5 h. The solvent was removed by distillation, and the tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (10.8 g) was used in the following reaction without further workup.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. customThe solvent was removed by distillation
  4. customthe tert-butyl 3-benzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (10.8 g) was used in the following reaction without further workup

Quellen und Nachweise

ORD-Eintrag
ord-a2d1db906421471b89f7d544cf88dcf8
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560468B2

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