Potassium Carbonate → (S)-4-Formylpiperazine-2-carboxylic acid tert-butylamide

HRID 1419519Notes

Reaction equation

HRID 1419519 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7]([NH:11][C:12]([C@@H:14]1[CH2:19][N:18]([CH:20]=[O:21])[CH2:17][CH2:16][N:15]1C(=O)C(F)(F)F)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O.C(O)C(C)C>[C:7]([NH:11][C:12]([C@@H:14]1[CH2:19][N:18]([CH:20]=[O:21])[CH2:17][CH2:16][NH:15]1)=[O:13])([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53801860(S)-4-Formyl-1-(trifluoroacetyl)piperazine-2-carboxylic acid tert-butylamide

Product 1

HCID 53948472(S)-4-Formylpiperazine-2-carboxylic acid tert-butylamideYield 136.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6560IsobutanolSolvent

Procedure

A solution of 25.5 g (184.5 mmol) of potassium carbonate in 130 ml of water was added to 15.0 g (48.5 mmol) of (S)-4-formyl-1-(trifluoroacetyl)-piperazine-2-carboxylic acid tert-butylamide in 130 ml of isobutyl alcohol and the mixture was heated at 60° to 65° C. for 1 hour. After phase separation, the aqueous phase was extracted with 100 ml of isobutyl alcohol and the combined organic phases were evaporated to give 14.10 g of the crude title compound (still containing solvent) in the form of a light yellow oil. Other data concerning the title compound was:

Workup

  1. temperaturethe mixture was heated at 60° to 65° C. for 1 hour
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted with 100 ml of isobutyl alcohol
  4. customthe combined organic phases were evaporated

Sources & evidence

ORD record
ord-38cdec802963459c962692e91d58865a
Source dataset
uspto-grants-1999_03
Patent number
US05886181

Reaction notes

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