Trifluoroacetic acid → HCID 22467120, compound

HRID 1934773Notes

Reaction equation

HRID 1934773 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[CH2:5][CH:6]1[C:10](=[O:11])[N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[S:7]1)[CH3:2].FC(F)(F)C(O)=O>C(Cl)Cl>[O:11]=[C:10]1[N:9]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2([CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[S:7][CH:6]1[CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22467148HCID 22467148, compound

Product 1

HCID 22467120HCID 22467120, compoundYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 56 ml of methylene chloride was dissolved 18.50 g of tert-butyl 2-(2-ethoxy-2-oxoethyl)-3-oxo-4-phenethyl-1-thia-4,8-diazaspiro[4.5]decane-8-carboxylate. After adding 56 ml of trifluoroacetic acid at 0-5° C., the resulting mixture was stirred at the same temperature as above for 30 minutes and then at ambient temperature for 5 hours. The solvent was distilled off under reduced pressure, the residue was poured into a mixture of ice water and ethyl acetate, pH was adjusted to 8.0 with saturated aqueous solution of sodium hydrogen carbonate, and the organic layer was separated. The organic layer was washed successively with water and saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. Thus, 7.26 g of ethyl 2-(3-oxo-4-phenethyl-1-thia-4,8-diazaspiro[4.5]decan-2-yl)-acetate was obtained as a yellow oily product.

Workup

  1. waitat ambient temperature for 5 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionthe residue was poured into a mixture of ice water and ethyl acetate, pH
  4. customthe organic layer was separated
  5. washThe organic layer was washed successively with water and saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-47dbaefbd30a4da8934c46bef56e4084
Source dataset
uspto-grants-2002_05
Patent number
US06384065B1

Reaction notes

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