Etodolac → (-)-Etodolac

HRID 2394816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2394816
[CH3:1][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]3[CH2:12][CH2:13][O:14][C:15]([CH2:18][C:19]([OH:21])=[O:20])([CH2:16][CH3:17])[C:10]=3[NH:9][C:8]=12.CNC[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O>C(O)C>[CH3:1][CH2:2][C:3]1[C:8]2[NH:9][C:10]3[C@:15]([CH2:18][C:19]([OH:21])=[O:20])([CH2:16][CH3:17])[O:14][CH2:13][CH2:12][C:11]=3[C:7]=2[CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 3308EtodolacHCID 8567N-Methyl-D-glucamine

Produkt 1

HCID 667528(-)-EtodolacAusbeute 53,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Racemic etodolac (1148 g) and N-methylglucamine (780.8 g) in ethanol (6.4 litres) were heated to 70° C. with stirring. The solution was cooled to 45° C. and then seeded with crystals of 100% ee (R)-etodolac meglumine salt and the mixture allowed to crystallise for 5 hours. The solid was filtered to provide (R)-etodolac (610 g, 86.4% ee) which could be recycled to racemic etodolac following the procedure in Example 2 below.

Aufarbeitung

  1. customto crystallise for 5 hours
  2. filtrationThe solid was filtered

Quellen und Nachweise

ORD-Eintrag
ord-aeab4212fa4d488b986950c881ddcb31
Quelldatensatz
uspto-grants-1998_09
Patentnummer
US05811558

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