(+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionic Acid Dihydrochloride → HCID 70074218, compound

HRID 1901371Notes

Reaction equation

HRID 1901371 reaction equation
[ClH:1].Cl.[C:3]([N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][C:27]([C:33](=[NH:35])[NH2:34])=[CH:28][CH:29]=4)[CH:24]=3)[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)(=[NH:5])[CH3:4]>O>[OH2:11].[OH2:11].[OH2:11].[OH2:11].[OH2:11].[ClH:1].[C:3]([N:6]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][C:27]([C:33](=[NH:34])[NH2:35])=[CH:28][CH:29]=4)[CH:24]=3)[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)(=[NH:5])[CH3:4]

Participants

3

Reactant 1

HCID 49796372(+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionic Acid Dihydrochloride

Product 1

HCID 70074218HCID 70074218, compoundYield 372.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

102.6 g of (+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionic acid dihydrochloride was dissolved in 1,000 ml of water. With stirring, the thus prepared solution was adjusted to pH 4.8 by gradually adding a strongly basic OH type ion exchange resin (Amberlite IRA-410). Thereafter, the resin was removed by filtration, and the resulting filtrate was concentrated to dryness. The thus obtained residue (94.6 g) was dissolved in 142 ml of water, and the solution was mixed with 1,570 ml of ethanol, and stirred at room temperature for 1 hour. After removing thus formed crystals by filtration, the resulting mother liquor was seeded with the crystals of interest, and stirred at 8° C. for 40 hours. Thereafter, the thus precipitated crystals were collected by suction filtration, washed with ethanol, and then air-dried for 6.5 hours under normal pressure at a relative humidity of 60 to 70%. In this way, 70.3 g of the title compound was obtained in the form of colorless prism crystals.

Workup

  1. additionby gradually adding a strongly basic OH type ion exchange resin (Amberlite IRA-410)
  2. customThereafter, the resin was removed by filtration
  3. concentrationthe resulting filtrate was concentrated to dryness
  4. dissolutionThe thus obtained residue (94.6 g) was dissolved in 142 ml of water
  5. additionthe solution was mixed with 1,570 ml of ethanol
  6. stirringstirred at room temperature for 1 hour
  7. customAfter removing thus formed crystals
  8. filtrationby filtration
  9. stirringstirred at 8° C. for 40 hours
  10. filtrationThereafter, the thus precipitated crystals were collected by suction filtration
  11. washwashed with ethanol
  12. customair-dried for 6.5 hours under normal pressure at a relative humidity of 60 to 70%

Sources & evidence

ORD record
ord-6ea3eaef91694ec3bdd95d344ff3cf72
Source dataset
uspto-grants-1996_11
Patent number
US05576343

Reaction notes

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