Sodium Hydroxide → HCID 178450340, compound

HRID 46481Notes

Reaction equation

HRID 46481 reaction equation
C(O)(=O)C.[CH2:5]([O:9][C:10]1[C:11]([O:44][CH3:45])=[C:12]([S:18]([NH:21][C@H:22]([C:30]([N:32]2[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH:33]2[C:39]([O:41]CC)=[O:40])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:29])[NH2:28])(=[O:20])=[O:19])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][CH2:7][CH3:8].[OH-].[Na+]>C(O)C.O>[CH2:5]([O:9][C:10]1[C:11]([O:44][CH3:45])=[C:12]([S:18]([NH:21][C@H:22]([C:30]([N:32]2[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH:33]2[C:39]([OH:41])=[O:40])=[O:31])[CH2:23][CH2:24][CH2:25][NH:26][C:27](=[NH:28])[NH2:29])(=[O:20])=[O:19])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:6][CH2:7][CH3:8]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178476285HCID 178476285, compound

Product 1

HCID 178450340HCID 178450340, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

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.

Workup

  1. distillationAt the end of this period, the reaction solvent was distilled off under reduced pressure at a temperature below 30° C
  2. dissolutionThe residue was dissolved in a small amount of water
  3. customto precipitate a white gummy substance
  4. customThe aqueous solution was separated by decantation
  5. dissolutionthe white precipitate was dissolved in 200 ml of chloroform
  6. washwashed with 30 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. customUpon evaporation of solvent

Sources & evidence

ORD record
ord-1f69e06d29c54012ad4942b49a985425
Source dataset
uspto-grants-1979_11
Patent number
US04173630

Reaction notes

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