HCID 70075059, compound → 3-(5-Amidino-2-benzofuranyl)-2-[4-[((3S)-3-pyrrolidinyl)oxy]phenyl]propionic Acid Dihydrochloride

HRID 1901368Notes

Reaction equation

HRID 1901368 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH2:14][CH:15]([C:21]3[CH:26]=[CH:25][C:24]([O:27][C@H:28]4[CH2:32][CH2:31][NH:30][CH2:29]4)=[CH:23][CH:22]=3)[C:16]([O:18]CC)=[O:17])=[CH:11][C:10]=2[CH:33]=1)(=[NH:5])[NH2:4]>Cl>[ClH:1].[ClH:1].[C:3]([C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([CH2:14][CH:15]([C:21]3[CH:22]=[CH:23][C:24]([O:27][C@H:28]4[CH2:32][CH2:31][NH:30][CH2:29]4)=[CH:25][CH:26]=3)[C:16]([OH:18])=[O:17])=[CH:11][C:10]=2[CH:33]=1)(=[NH:4])[NH2:5]

Participants

3

Reactant 1

HCID 70075059HCID 70075059, compound

Product 1

HCID 700725263-(5-Amidino-2-benzofuranyl)-2-[4-[((3S)-3-pyrrolidinyl)oxy]phenyl]propionic Acid DihydrochlorideYield 82.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

3.2 g of ethyl 3-(5-amidino-2-benzofuranyl)-2-[4-[((3S)-3-pyrrolidinyl)oxy]phenyl]propionate dihydrochloride was dissolved in 80 ml of 2N hydrochloric acid, and the solution was refluxed under heating for 30 minutes. After cooling and distilling off the solvent, the resulting residue was purified by subjecting it to column chromatography using a column packed with a highly porous polymer type synthetic adsorbent (styrene-divinylbenzene polymer: Diaion HP-20) and using 5-10% acetonitrile as an elution solvent. Thereafter, the thus eluted fractions of interest were pooled, adjusted to pH 2-3 with dilute hydrochloric acid, and then concentrated to dryness. In this way, 1.25 g of the title compound was obtained in a solid form.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureunder heating for 30 minutes
  3. temperatureAfter cooling
  4. distillationdistilling off the solvent
  5. customthe resulting residue was purified
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9bd56541bb3c43b995ad8baedc12ab91
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

Loading…