Potassium Carbonate → Jtp-4819

HRID 1735392Notes

Reaction equation

HRID 1735392 reaction equation
C([O:4][CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:14])=[O:7])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.CO>[OH:4][CH2:5][C:6]([C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13]([C@@H:15]1[CH2:19][CH2:18][CH2:17][N:16]1[C:20]([NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21])=[O:14])=[O:7]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 15389023(S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide

Product 1

HCID 178060Jtp-4819Yield 30.2%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

(S)-2-[[(S)-2-(Acetoxyacetyl)-1-pyrrolidinyl]carbonyl]-N-(phenylmethyl)-1-pyrrolidinecarboxamide (3.0 g) obtained in Example 1 was dissolved in water-methanol (1:1, 30 ml) and anhydrous potassium carbonate (1.14 g) were added under ice-cooling. The mixture was stirred at room temperature for 1 hour, and the reaction mixture was concentrated. Methylene chloride was added and the mixture was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was dissolved in ethyl acetate, added with active charcoal, stirred at room temperature for 30 minutes, filtered and concentrated to give the title compound (0.81 g) (see Table 1).

Workup

  1. temperaturecooling
  2. concentrationthe reaction mixture was concentrated
  3. additionMethylene chloride was added
  4. washthe mixture was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. additionadded with active charcoal
  9. stirringstirred at room temperature for 30 minutes
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-928345c2dcde4dbeb0cd19216e893863
Source dataset
uspto-grants-1996_07
Patent number
US05536737

Reaction notes

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