Benzyl Chloride → 1-benzyl-8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

HRID 552341Notes

Reaction equation

HRID 552341 reaction equation
[CH2:1]([CH:3]([CH2:21][CH3:22])[C:4]([N:6]1[CH2:20][CH2:19][C:9]2([NH:13][C:12](=[O:14])[C@H:11]([CH2:15][CH2:16][S:17][CH3:18])[NH:10]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].[CH2:25](Cl)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[NH4+].[Cl-]>C1COCC1>[CH2:25]([N:13]1[C:9]2([CH2:8][CH2:7][N:6]([C:4](=[O:5])[CH:3]([CH2:1][CH3:2])[CH2:21][CH3:22])[CH2:20][CH2:19]2)[NH:10][C@@H:11]([CH2:15][CH2:16][S:17][CH3:18])[C:12]1=[O:14])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7503Benzyl ChlorideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 671656138-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

Product 1

HCID 671652761-benzyl-8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one (420 mg, 1.3 mmol) in 20 mL of dry THF there was added sodium hydride (50 mg, 1.9 mmol) at 0° C. and under a blanket of nitrogen. Following stirring over a period of 1 h at 0° C., benzyl chloride (140 mg, 1.4 mmol) was slowly added dropwise and the mixture was then heated under reflux over a period of 24 h. Following the addition of an aqueous saturated NH4Cl solution (15 mL), the reaction mixture was isolated by filtration and the filtrate was extracted with EE (3×10 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-benzyl-8-(2-ethylbutyryl)-3-(S)-(2-methylsulfanylethyl)-1,4,8-triazaspiro[4,5]decan-2-one was obtained in a yield of 239 mg (45%).

Workup

  1. temperaturethe mixture was then heated
  2. temperatureunder reflux over a period of 24 h
  3. customthe reaction mixture was isolated by filtration
  4. extractionthe filtrate was extracted with EE (3×10 mL)
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. customremoval
  7. distillationby distillation
  8. customof the solvent, there was obtained the crude product as a yellow oil
  9. customFurther purification

Sources & evidence

ORD record
ord-384ef759f8044fb59b8b3fa24c3404f7
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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