Etodolac → (-)-Etodolac

HRID 2394816Notes

Reaction equation

HRID 2394816 reaction equation
[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

Participants

4

Reactant 2

HCID 3308EtodolacHCID 8567N-Methyl-D-glucamine

Product 1

HCID 667528(-)-EtodolacYield 53.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
45 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-aeab4212fa4d488b986950c881ddcb31
Source dataset
uspto-grants-1998_09
Patent number
US05811558

Reaction notes

Loading…