Hydrochloric Acid → HCID 67165601, compound

HRID 552337Notes

Reaction equation

HRID 552337 reaction equation
[CH2:1]([C@@H:8]1[NH:12][C:11]2([CH2:17][CH2:16][N:15]([C:18](=[O:24])[CH:19]([CH2:22][CH3:23])[CH2:20][CH3:21])[CH2:14][CH2:13]2)[NH:10][C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:28](Cl)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.Cl>C1COCC1>[CH2:28]([N:10]1[C:11]2([CH2:17][CH2:16][N:15]([C:18](=[O:24])[CH:19]([CH2:20][CH3:21])[CH2:22][CH3:23])[CH2:14][CH2:13]2)[NH:12][C@@H:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9]1=[O:25])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 11256413HCID 11256413, compound

Product 1

HCID 67165601HCID 67165601, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(S)-benzyl-8-(2-ethylbutyryl)-1,4,8-triazaspiro[4,5]decan-2-one (1.0 g, 2.9 mmol) in 40 mL of dry THF there was added sodium hydride (90 mg, 3.8 mmol) at room temperature and under a blanket of nitrogen. Following stirring over a period of 1 h at RT benzyl chloride (1.47 g, 11.6 mmol) was slowly added dropwise and the mixture was then heated over a period of 12 h under reflux. Following the addition of an aqueous saturated HCl solution (20 mL), the reaction mixture was isolated by filtration and the filtrate was extracted with EE (3×15 mL), and the combined organic phases were dried over Na2SO4. Following removal, by distillation, of the solvent, there was obtained the crude product as a yellow oil. Further purification was carried out by column chromatography. The product 1,3-(S)-dibenzyl-8-(2-ethylbutyryl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 1.1 g (52%).

Workup

  1. additionwas slowly added dropwise
  2. temperaturethe mixture was then heated over a period of 12 h
  3. temperatureunder reflux
  4. customthe reaction mixture was isolated by filtration
  5. extractionthe filtrate was extracted with EE (3×15 mL)
  6. dry with materialthe combined organic phases were dried over Na2SO4
  7. customremoval
  8. distillationby distillation
  9. customof the solvent, there was obtained the crude product as a yellow oil
  10. customFurther purification

Sources & evidence

ORD record
ord-e152087183e64a559809a0dbffa64905
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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