Deferoxamine → Deferoxamine Mesylate

HRID 24975

Reaction equation

HRID 24975 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].[CH3:40][S:41]([OH:44])(=[O:43])=[O:42]>C(O)C.O>[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].[CH3:40][S:41]([OH:44])(=[O:43])=[O:42]

Participants

5

Reactant 2

HCID 2973Deferoxamine2×HCID 6395Methanesulfonic Acid

Product 1

HCID 62881Deferoxamine Mesylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

The deferoxamine B base was then suspended in a mixture of ethanol (3.1 L) and water (0.46 L). Methanesulfonic acid was slowly added until the deferoxamine B base dissolved and the solution reached a pH of 3.5. Another 30 L of ethanol was added to the solution to precipitate deferoxamine B mesylate. The resulting suspension was then cooled to between −5° C. and 0° C. and maintained at reduced temperature for 24 h. The crystals were isolated by filtration, washed with ethanol and dried under vacuum to yield deferoxamine B mesylate (299 g) with a purity of 98% (w/w) as determined by HPLC analysis.

Workup

  1. dissolutiondissolved
  2. customto precipitate deferoxamine B mesylate
  3. temperatureThe resulting suspension was then cooled to between −5° C. and 0° C.
  4. temperaturemaintained
  5. customfor 24 h
  6. customThe crystals were isolated by filtration
  7. washwashed with ethanol
  8. customdried under vacuum

Sources & evidence

ORD record
ord-0224a31cbf1f4feab1a91519dee50bfe
Source dataset
uspto-grants-2005_02
Patent number
US06858414B2

Linked notes

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