Atenolol → Atenolol p-toluate

HRID 1589041

Reaktionsgleichung

Reaktionsgleichung von HRID 1589041
[CH3:1][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:3].[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=1>CC(C)=O>[CH3:3][CH:2]([NH:4][CH2:5][CH:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:1].[C:21]1([CH3:20])[CH:26]=[CH:25][C:24]([C:27]([O-:29])=[O:28])=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 2249AtenololHCID 7470P-Toluic Acid

Produkt 1

HCID 86745986Atenolol p-toluateAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

The atenolol having low optical purity (1 mole) and p-toluic acid (1 mole) are dissolved in acetone (5 to 50 liters) with heating and the mixture is stirred at 0° to 15° C. for 5 to 24 hours. The precipitated crystals are removed by filtration, and the mother liquor is concentrated to give an optically active atenolol p-toluate with having higher optical purity, for example a salt having an optical purity of 98% ee or more from a salt having an optical purity of 91% ee in a yield of 50 to 80%. In this method, when benzoic acid is used instead of p-toluic acid and chloroform is used instead of acetone, similar result is obtained. When p-t-butylbenzoic acid is used instead of p-toluic acid in the above method, the produced salt is hardly soluble in a solvent, and hence, it is necessary to use a solvent having higher solubility such as ethanol or 2-propanol instead of acetone.

Aufarbeitung

  1. temperaturewith heating
  2. customThe precipitated crystals are removed by filtration
  3. concentrationthe mother liquor is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-90ce5b4de57142c19941570169cf67c1
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05223646

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