Trifluoroacetic acid → 1-Benzyl-3-(2-methylsulfanyl-ethyl)-1,4,8-triazaspiro[4,5]decan-2-one

HRID 227265Notes

Reaction equation

HRID 227265 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([N:15]1[C:19]2([CH2:24][CH2:23][N:22](C(OCCCC)=O)[CH2:21][CH2:20]2)[NH:18][CH:17]([CH2:32][CH2:33][S:34][CH3:35])[C:16]1=[O:36])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:8]([N:15]1[C:19]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:18][CH:17]([CH2:32][CH2:33][S:34][CH3:35])[C:16]1=[O:36])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 688392811-Butyl benzyl-3-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate

Product 1

HCID 684475881-Benzyl-3-(2-methylsulfanyl-ethyl)-1,4,8-triazaspiro[4,5]decan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (7.8 g, 68.0 mmol) was added dropwise to a solution of tert 1-butyl benzyl-3-(2-methylsulfanylethyl)-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (1.5 g, 3.5 mmol) in CH2Cl2 (10 ml) at 0° C. and the mixture was stirred for 15 min at this temperature. After warming to RT, the reaction solution was stirred for a further 2.5 h. Subsequently, the reaction solution was adjusted to pH 7 to 8 using saturated aqueous NaHCO3 solution, the organic phase was separated off, and the aqueous phase was extracted with CH2Cl2 (2×10 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was removed by distillation. Workup was carried out by means of column chromatography to give 1-benzyl-3-(2-methylsulfanyl-ethyl)-1,4,8-triazaspiro[4,5]decan-2-one in a yield of 655 mg (58% of theory).

Workup

  1. stirringthe reaction solution was stirred for a further 2.5 h
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×10 ml)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-2067ea6136de442f85a6884df7976588
Source dataset
uspto-grants-2009_07
Patent number
US07560468B2

Reaction notes

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