Reaction #94591

Reaction equation

ethyl 1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate acetate

→

1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid

Yield 73.4%

Solvents

chloroform

—

N-NaOH

ethanol

Conditions

Workup

1. 1
   ConcentrationThen, the reaction mixture was concentrated
2. 2
   workup.DISSOLUTIONdissolved in 10 ml of water
3. 3
   Otherto give a white gummy precipitate which
4. 4
   WashThe chloroform solution was washed with saturated NaCl solution
5. 5
   Dryingdried over anhydrous sodium sulfate
6. 6
   Otherevaporated in vacuo

Procedure

A solution of 2.4 g of ethyl 1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylate acetate in 10 ml of ethanol and 10 ml of N-NaOH solution was stirred overnight at room temperature. Then, the reaction mixture was concentrated and dissolved in 10 ml of water. The solution was neutralized with 2N-HCl solution to give a white gummy precipitate which was dissolved in 150 ml of chloroform. The chloroform solution was washed with saturated NaCl solution, dried over anhydrous sodium sulfate and evaporated in vacuo to give 1.52 g of 1-[N2 -(3-cyclohexyl-4-methoxyphenylsulfonyl)-L-arginyl]-4-methyl-2-piperidinecarboxylic acid as an amorphous solid. I.R. (KBr): 3350, 2920, 1620, 1250 cm-1.

Source