Reaction #74759

Reaction equation

ethyl 1-[N2 -(3-butoxy-2,4-dimethoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate acetate

NaOH

→

1-[N2 -(3-butoxy2,4-dimethoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid

Yield 79.6%

Solvents

ethanol

water

Conditions

Workup

1. 1
   workup.DISTILLATIONAt the end of this period, the reaction solvent was distilled off under reduced pressure at a temperature below 30° C
2. 2
   workup.DISSOLUTIONThe residue was dissolved in a small amount of water
3. 3
   Otherto precipitate a white gummy substance
4. 4
   OtherThe aqueous solution was separated by decantation
5. 5
   workup.DISSOLUTIONthe white precipitate was dissolved in 200 ml of chloroform
6. 6
   Washwashed with 30 ml of water
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   OtherUpon evaporation of solvent

Procedure

To a solution of 5.8 g of ethyl 1-[N2 -(3-butoxy-2,4-dimethoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate acetate in 80 ml of ethanol and 40 ml of water was added 10 ml of 2N NaOH aqueous solution at room temperature and stirring was continued overnight at room temperature. At the end of this period, the reaction solvent was distilled off under reduced pressure at a temperature below 30° C. The residue was dissolved in a small amount of water and then neutralized with 2N NCl to precipitate a white gummy substance. The aqueous solution was separated by decantation and the white precipitate was dissolved in 200 ml of chloroform, washed with 30 ml of water and then dried over anhydrous sodium sulfate. Upon evaporation of solvent, there was obtained 4.0 g (79%) of 1-[N2 -(3-butoxy2,4-dimethoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid in the form of an amorphous solid.

Source