Water → Deferoxamine Mesylate

HRID 24974Notes

Reaction equation

HRID 24974 reaction equation
[CH3:1][C:2]([N:4]([OH:39])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([CH2:13][CH2:14][C:15]([N:17]([OH:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][CH2:27][C:28]([N:30]([OH:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:29])=[O:25])=[O:16])=[O:12])=[O:3].O.[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]>C(O)C>[CH3:1][C:2]([N:4]([OH:39])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][NH:10][C:11]([CH2:13][CH2:14][C:15]([N:17]([OH:38])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24]([CH2:26][CH2:27][C:28]([N:30]([OH:37])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:29])=[O:25])=[O:16])=[O:12])=[O:3].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]

Participants

5

Reactant 3

HCID 962WaterHCID 2973DeferoxamineHCID 6395Methanesulfonic Acid

Product 1

HCID 62881Deferoxamine Mesylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-10 °C

Procedure

The deferoxamine free base was suspended in a 14:3 mixture of ethanol and water (42.5 L). Dilute methanesulfonic acid was slowly added to the suspension until the free base dissolved and the solution attained a pH of between 3.7 and 5. Ethanol (200 L) was added to the solution to precipitate the mesylate salt and the resulting suspension was cooled to −10° C. and maintained at −10° C. for several hours. The resulting crystals were isolated by filtration, washed with ethanol (50 L) and dried under vacuum to yield 3.4 kg of deferoxamine mesylate. HPLC chromatography showed that the mesylate contained 1.84 weight % impurities. The moisture content as determined by Karl-Fischer Analysis was 0.2 mole %. USP/NF 24/19, pp. 2003-2004 (1999). Coloration was better than Y5 as measured according to the European Pharmacopeia criteria for grading coloration.

Workup

  1. dissolutiondissolved
  2. customto precipitate the mesylate salt
  3. temperaturemaintained at −10° C. for several hours
  4. customThe resulting crystals were isolated by filtration
  5. washwashed with ethanol (50 L)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-4842602b9ad14045b253873d24ba47c9
Source dataset
uspto-grants-2005_02
Patent number
US06858414B2

Reaction notes

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