Water → HCID 67166130, compound

HRID 552347Notes

Reaction equation

HRID 552347 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].C(N(CC)CC)C.Cl.[NH2:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH2:26][S:27][CH3:28].O>CCO.C(Cl)Cl>[CH3:28][S:27][CH2:26][CH2:25][C@@H:24]1[NH:23][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:31][C:29]1=[O:30]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 7577838tert-Butyl 2-oxopiperidine-1-carboxylateHCID 18531008(2S)-2-amino-4-(methylsulfanyl)butanamide hydrochloride

Product 1

HCID 67166130HCID 67166130, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

N-tert-Butyloxycarbonylpiperidone (5.9 g, 29.8 mmol) and triethylamine (3.02 g, 29.8 mmol) were added to a solution of (S)-methioninamide hydrochloride (5.5 g, 29.8 mmol) in dry EtOH (66 ml) and the mixture was heated for 2.5 h under reflux. After addition of water (50 ml) and CH2Cl2 (200 ml), the organic phase was separated off and the aqueous phase was extracted with CH2Cl2 (3×20 ml). The combined organic phases were dried over Na2SO4. After filtration, the solvent was distilled off. tert-Butyl 3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate was obtained in a yield of 8.0 g (82%).

Workup

  1. temperaturethe mixture was heated for 2.5 h
  2. temperatureunder reflux
  3. customthe organic phase was separated off
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×20 ml)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. filtrationAfter filtration
  7. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c839254cc0af4e54bd2c0a8b77fd5072
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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