Ketorolac → Ketorolac Tromethamine

HRID 636080

Reaction equation

HRID 636080 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:6]=1.[NH2:20][C:21]([CH2:26][OH:27])([CH2:24][OH:25])[CH2:22][OH:23]>C(O)(C)C.O>[CH:1]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[N:13]3[CH2:14][CH2:15][CH:16]([C:17]([OH:19])=[O:18])[C:12]3=[CH:11][CH:10]=2)=[O:8])=[CH:3][CH:2]=1.[CH2:22]([OH:23])[C:21]([NH2:20])([CH2:26][OH:27])[CH2:24][OH:25]

Participants

5

Reactant 2

HCID 3826KetorolacHCID 6503Tris(hydroxymethyl)aminomethane

Product 1

HCID 84003Ketorolac Tromethamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
40 °C

Procedure

Ketorolac acid (20 gm, Abbott Laboratories) is dissolved in 156.0 gm of isopropanol. A solution of 12.0 gm of tromethamine in 25.0 gm of water is added, and the mixture is heated to 40° C. to a solution. The solution is filtered through a 0.2 micron filter. To the clear filtrate is added 356.0 gm of ethyl acetate, and the ternary solution is distilled under vacuum to approximately half the volume. Another aliquot of 356.0 gm of ethyl acetate is added and the mixture distilled to approximately half the volume and solid starts precipitating out. Ethyl acetate (356.0 gm) is added once more and the mixture distilled to approximately half the volume. The solution is cooled to 10° C. and the solid ketorolac tromethamine is isolated by filtration. The collected solids are dried under vacuum to afford the desired product.

Workup

  1. filtrationThe solution is filtered through a 0.2 micron
  2. filtrationfilter
  3. additionTo the clear filtrate is added 356.0 gm of ethyl acetate
  4. distillationthe ternary solution is distilled under vacuum to approximately half the volume
  5. additionAnother aliquot of 356.0 gm of ethyl acetate is added
  6. distillationthe mixture distilled to approximately half the volume and solid starts
  7. customprecipitating out
  8. additionEthyl acetate (356.0 gm) is added once more
  9. distillationthe mixture distilled to approximately half the volume
  10. temperatureThe solution is cooled to 10° C.

Sources & evidence

ORD record
ord-98ee12f946b940189a81b7e69a78b47e
Source dataset
uspto-grants-2001_02
Patent number
US06191285B1

Linked notes

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