Benzyl Chloride → tert-butyl 1-benzyl-3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

HRID 552349Notes

Reaction equation

HRID 552349 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][C@@H:5]1[NH:9][C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[NH:7][C:6]1=[O:22].[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:7]1[C:8]2([CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:19])([CH3:21])[CH3:20])=[O:16])[CH2:11][CH2:10]2)[NH:9][C@@H:5]([CH2:4][CH2:3][S:2][CH3:1])[C:6]1=[O:22])[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 67166130tert-Butyl 3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Product 1

HCID 67165908tert-butyl 1-benzyl-3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyl 3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro-[4,5]decane-8-carboxylate (4.4 g, 13.4 mmol) in THF (72 ml) was added dropwise at 0° C. to a suspension of NaH (385 mg, 16.0 mmol) in THF (60 ml). After stirring for 1 h at 0° C., benzyl chloride (2.0 g, 16.0 mmol) was added dropwise, and the mixture was allowed to warm to RT and was heated for 68 h under reflux. The reaction mixture was treated with aqueous saturated NH4Cl solution (20 ml), the organic phase was separated off and the aqueous phase was extracted with EA (3×50 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was distilled off. The workup was carried out by means of column chromatography and afforded tert-butyl 1-benzyl-3-(S)-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate in a yield of 1.6 g (30%).

Workup

  1. temperatureto warm to RT
  2. temperaturewas heated for 68 h
  3. temperatureunder reflux
  4. customthe organic phase was separated off
  5. extractionthe aqueous phase was extracted with EA (3×50 ml)
  6. dry with materialThe combined organic phase was dried over Na2SO4
  7. filtrationfiltered
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-ebe92862ea94440fbc7f5bd5953b7bfa
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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