HCID 131720735, compound → HCID 131720738, compound

HRID 964986Notes

Reaction equation

HRID 964986 reaction equation
[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][N:14]([C@H:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]([O:26]CC)=[O:25])[CH2:19][C@H:18]3[CH2:29][C:30]([O:32]CC)=[O:31])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)(=[NH:4])[NH2:3]>Cl>[ClH:1].[ClH:1].[ClH:1].[C:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:12][CH2:13][N:14]([C@H:17]3[CH2:22][CH2:21][N:20]([CH2:23][C:24]([OH:26])=[O:25])[CH2:19][C@H:18]3[CH2:29][C:30]([OH:32])=[O:31])[CH2:15][CH2:16]2)=[CH:7][CH:6]=1)(=[NH:3])[NH2:4]

Participants

3

Reactant 1

HCID 131720735HCID 131720735, compound

Product 1

HCID 131720738HCID 131720738, compoundYield 165.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

280 mg of (+)-cis-diethyl 4-[4-(4-amidinophenyl)-1-piperazinyl]-1,3-piperidinediacetate hydrochloride was dissolved in 10 ml of 1N-hydrochloric acid and refluxed for 48 hours. The reaction liquid was distilled, and the resulting residue was purified by ODS column chromatography (using an eluent of water) to obtain 160 mg of (+)-cis-4-[4-(4-amidinophenyl)-1-piperazinyl]-1,3-piperidinediacetic acid trihydrochloride (98.2% e.e.).

Workup

  1. temperaturerefluxed for 48 hours
  2. customThe reaction liquid
  3. distillationwas distilled
  4. customthe resulting residue was purified by ODS column chromatography (

Sources & evidence

ORD record
ord-0789858e25f54e55926cf2105e040ae8
Source dataset
uspto-grants-1998_06
Patent number
US05773442

Reaction notes

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