Ketorolac → Ketorolac Tromethamine

HRID 430838

Reaction equation

HRID 430838 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]>CO>[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

4

Reactant 2

HCID 3826KetorolacHCID 6503Tris(hydroxymethyl)aminomethane

Product 1

HCID 84003Ketorolac TromethamineYield 95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ketorolac (25 g) and 11.9 g tromethamine were dissolved in 175 mL methanol. The solution was filtered and the filter washed with 40 mL methanol. The resulting solution was concentrated by vacuum distillation. Ethyl acetate (1×172 mL), (1×200 mL) was added to the solution to precipitate the ketorolac tromethamine; and the solution was cooled to room temperature for two hours, cooled further to 0° C., and filtered. The precipitate was washed with ethyl acetate/methanol (4:1 v/v) and dried under vacuum at a temperature of approximately 65° C., to yield ketorolac tromethamine (35.0 g, 95% yield).

Workup

  1. filtrationThe solution was filtered
  2. washthe filter washed with 40 mL methanol
  3. concentrationThe resulting solution was concentrated by vacuum distillation
  4. additionEthyl acetate (1×172 mL), (1×200 mL) was added to the solution
  5. customto precipitate the ketorolac tromethamine
  6. temperaturecooled further to 0° C.
  7. filtrationfiltered
  8. washThe precipitate was washed with ethyl acetate/methanol (4:1 v/v)
  9. customdried under vacuum at a temperature of approximately 65° C.

Sources & evidence

ORD record
ord-7131ab8fd67246ca9e7cf7b323a51439
Source dataset
uspto-grants-2001_11
Patent number
US06323344B1

Linked notes

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