Metoprolol → (S)-Metoprolol

HRID 1087281

Reaktionsgleichung

Reaktionsgleichung von HRID 1087281
[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][CH2:16][O:17][CH3:18])=[CH:13][CH:14]=1)[CH3:3].C(O)(=O)/C=C/C=C/C>CC(C)=O>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][O:17][CH3:18])=[CH:13][CH:14]=1)[CH3:1]

Komponenten

4

Edukt 2

HCID 4171MetoprololHCID 643460Sorbic Acid

Produkt 1

HCID 157716(S)-MetoprololAusbeute 115,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the stirred acetone solution of metoprolol base (19.3 mol), acetone (30 l) and sorbic acid (2.12 kg, 18.9 mol) were added at room temperature. The mixture was heated to reflux and the hot solution was filtered. The filtrate was allowed to cool slowly to 0° C. The crystals were centrifugated off, washed with cold acetone (10 l) and dried for three days in vacuo at room temperature to yield 5.95 kg of crystalline (S)-metoprolol. (81% from (4)).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationthe hot solution was filtered
  4. washwashed with cold acetone (10 l)
  5. customdried for three days in vacuo at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-ecc3204946d546b58f26672c8d79018c
Quelldatensatz
uspto-grants-1991_07
Patentnummer
US05034535

Verknüpfte Notizen

Wird geladen…