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

HRID 1738716Notes

Reaction equation

HRID 1738716 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]([CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][C:29]([C:35](=[NH:37])[NH2:36])=[CH:30][CH:31]=4)[CH:26]=3)[C:19]([O:21]CC)=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)(=[NH:5])[CH3:4]>Cl>[ClH:1].[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]([CH2:24][C:25]3[CH:34]=[CH:33][C:32]4[C:27](=[CH:28][C:29]([C:35](=[NH:36])[NH2:37])=[CH:30][CH:31]=4)[CH:26]=3)[C:19]([OH:21])=[O:20])=[CH:14][CH:13]=2)[CH2:7]1)(=[NH:5])[CH3:4]

Participants

3

Reactant 1

HCID 86750015Ethyl (+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionate Dihydrochloride

Product 1

HCID 49796372(+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionic Acid DihydrochlorideYield 198.4%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

While keeping the inner temperature at -5° C. or below, 110.1 g of ethyl (+)-2-[4-[((3S)-1-acetimidoyl-3-pyrrolidinyl)oxy]phenyl]-3-(7-amidino-2-naphthyl)propionate dihydrochloride was dissolved in 3,300 ml of concentrated hydrochloric acid, and the resulting solution was allowed to stand still for 232 hours at 5° C. The resulting reaction solution was concentrated by distilling off hydrochloric acid and water under a reduced pressure. 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 a water/acetonitrile mixture as an elution solvent. Thereafter, the thus eluted fractions of interest were pooled, mixed with a small amount of dilute hydrochloric acid, and then concentrated to dryness. In this way, 103.6 g of the title compound was obtained in the form of a light yellow solid.

Workup

  1. customat -5° C. or below
  2. customThe resulting reaction solution
  3. concentrationwas concentrated
  4. distillationby distilling off hydrochloric acid and water under a reduced pressure
  5. customThe resulting residue was purified
  6. additionmixed with a small amount of dilute hydrochloric acid
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-a97c4d2e00284b7d885e08716c206f91
Source dataset
uspto-grants-1999_10
Patent number
US05962695

Reaction notes

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