Hydrochloric Acid → HCID 67690311, compound

HRID 964983Notes

Reaction equation

HRID 964983 reaction equation
[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:19][CH:18]3[CH2:29][CH2:30][C:31]([O:33]CC)=[O:32])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3].[OH-].[Na+].Cl>C(O)C>[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][CH:18]3[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[CH2:15][CH2:16]2)=[CH:7][CH:6]=1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22444742HCID 22444742, compound

Product 1

HCID 67690311HCID 67690311, compoundYield 57.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

350 mg of ethyl 4-[4-(4-amidinophenyl)-1-piperazinyl]-1-ethoxycarbonylmethyl-3-piperidinepropionate hydrochloride was dissolved in 20 ml of ethanol, and 2.5 ml of an aqueous solution of 1N-sodium hydroxide was added thereto and stirred at room temperature for 5 hours. 2.5 ml of 1N-hydrochloric acid was added to the reaction liquid, from which the solvent was removed by distillation. The resulting residue was purified by HP-20 column chromatography (using a gradient eluent of water to water/ethanol=50/1) to obtain 180 mg of 4-[4-(4-amidinophenyl)-1-piperazinyl)-1-carboxymethyl-3-piperidinepropionic acid hydrochloride.

Workup

  1. customwas removed by distillation
  2. customThe resulting residue was purified by HP-20 column chromatography (

Sources & evidence

ORD record
ord-420e0acc59354473bfd8de2e486e85d1
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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