Triethylamine → HCID 67165613, compound

HRID 552335Notes

Reaction equation

HRID 552335 reaction equation
[CH2:1]([CH:3]([CH2:13][CH3:14])[C:4]([N:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].Cl.[NH2:16][C@H:17]([C:22]([NH2:24])=[O:23])[CH2:18][CH2:19][S:20][CH3:21].C(N(CC)CC)C>CCO>[CH2:1]([CH:3]([CH2:13][CH3:14])[C:4]([N:6]1[CH2:11][CH2:10][C:9]2([NH:24][C:22](=[O:23])[C@H:17]([CH2:18][CH2:19][S:20][CH3:21])[NH:16]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 18531008(2S)-2-amino-4-(methylsulfanyl)butanamide hydrochlorideHCID 24710387HCID 24710387, compound

Product 1

HCID 67165613HCID 67165613, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(2-ethylbutyryl)-piperidin-4-one (1.6 g, 8.1 mmol), (S)-methioninamide hydrochloride (1.5 g, 8.1 mmol), and triethylamine (820 mg, 8.1 mmol) in EtOH (66 mL) was heated under reflux over a period of 16 h. Following removal of the solvent, water (50 mL) and CH2Cl2 (50 mL) were added to the residue and the mixture was basified with concentrated sodium hydroxide solution. The aqueous phase was extracted with CH2Cl2 (3×20 mL) and the combined organic phases were dried over Na2SO4. Following removal of the solvent and vacuum drying, there was obtained the product 8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5-]-decan-2-one in a yield of 1.8 g (69%).

Workup

  1. temperatureunder reflux over a period of 16 h
  2. customremoval of the solvent, water (50 mL) and CH2Cl2 (50 mL)
  3. additionwere added to the residue
  4. extractionThe aqueous phase was extracted with CH2Cl2 (3×20 mL)
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. customremoval of the solvent and vacuum
  7. customdrying

Sources & evidence

ORD record
ord-46cdc0a7f95b4ffdabf30cb12392801d
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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