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

HRID 227253

Reaction equation

HRID 227253 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a2d1db906421471b89f7d544cf88dcf8
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Linked notes

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