Tris(hydroxymethyl)aminomethane → Meloxicam trometamol

HRID 2212813Notes

Reaction equation

HRID 2212813 reaction equation
[NH2:1][C:2]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:3][OH:4].[CH3:9][C:10]1[S:14][C:13]([NH:15][C:16]([C:18]2[N:29]([CH3:30])[S:26](=[O:28])(=[O:27])[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:19]=2[OH:31])=[O:17])=[N:12][CH:11]=1>C(O)C>[CH3:9][C:10]1[S:14][C:13]([NH:15][C:16]([C:18]2[N:29]([CH3:30])[S:26](=[O:27])(=[O:28])[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:19]=2[OH:31])=[O:17])=[N:12][CH:11]=1.[NH2:1][C:2]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 6503Tris(hydroxymethyl)aminomethane2×HCID 54677470Meloxicam

Product 1

HCID 86587442Meloxicam trometamolYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 0.4 L of ethanol, there was added 2.42 g (20 mM) of trometamol and the resulting mixture was heated to 80° C. To the resulting trometamol solution, there was added 7.03 g (20 mM) of meloxicam and the resulting mixture was stirred for one hour, while maintaining the temperature of the mixture at 80° C. The solution was filtered while it was still hot, cooled to room temperature and then concentrated to dryness under reduced pressure. Cold ethanol (100 mL) was added to the resulting yellow solid residue and then the solid mass of the residue was triturated. The precipitates were subjected to suction filtration and the resulting crystalline powder was dried under reduced pressure to give 9.13 g (yield 97%) of meloxicam trometamol salt.

Workup

  1. temperaturewhile maintaining the temperature of the mixture at 80° C
  2. filtrationThe solution was filtered while it
  3. temperaturecooled to room temperature
  4. concentrationconcentrated to dryness under reduced pressure
  5. additionCold ethanol (100 mL) was added to the resulting yellow solid residue
  6. customthe solid mass of the residue was triturated
  7. filtrationThe precipitates were subjected to suction filtration
  8. customthe resulting crystalline powder was dried under reduced pressure

Sources & evidence

ORD record
ord-39f335226ff04835b2b1a9db5df1969f
Source dataset
uspto-grants-2006_09
Patent number
US07105512B2

Reaction notes

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