Methanesulfonic Acid → Eprosartan Mesylate

HRID 1808663

Reaction equation

HRID 1808663 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][CH:16]=2)[C:8](/[CH:20]=[C:21](/[C:28]([OH:30])=[O:29])\[CH2:22][C:23]2[S:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][N:6]=1.[CH3:31][S:32]([OH:35])(=[O:34])=[O:33]>C(O)(C)C>[CH3:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[CH:15][CH:16]=2)[C:8](/[CH:20]=[C:21](/[C:28]([OH:30])=[O:29])\[CH2:22][C:23]2[S:27][CH:26]=[CH:25][CH:24]=2)=[CH:7][N:6]=1.[CH3:31][S:32]([OH:35])(=[O:34])=[O:33]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 5281037Eprosartan

Product 1

HCID 5282474Eprosartan Mesylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
8 °C

Procedure

As per the process described and exemplified in the U.S. Pat. No. 5,185,351 (herein after referred to as the '351 patent), eprosartan free base (obtained as per the processes described in example I of the '351 patent) is suspended in isopropyl alcohol under stirring at about 8° C., methanesulfonic acid is added rapidly to the stirred suspension, the mass cooled to 3° C. and the precipitated solid collected to give crude eprosartan mesylate. The crude eprosartan mesylate is further purified by dissolving crude eprosartan mesylate in acetic acid at 80° C., filtered through a hyflow bed at 80° C., the solution cooled slowly to 25° C. followed by stirring and then the precipitated solid is collected by adding ethyl acetate as an anti-solvent to give eprosartan mesylate.

Workup

  1. customobtained as per the processes
  2. temperaturethe mass cooled to 3° C.
  3. customthe precipitated solid collected
  4. customto give crude eprosartan mesylate
  5. customThe crude eprosartan mesylate is further purified
  6. dissolutionby dissolving crude eprosartan mesylate in acetic acid at 80° C.
  7. filtrationfiltered through a hyflow bed at 80° C.
  8. temperaturethe solution cooled slowly to 25° C.
  9. stirringby stirring
  10. customthe precipitated solid is collected
  11. additionby adding ethyl acetate as an anti-solvent

Sources & evidence

ORD record
ord-aaf8478e97c44019b00c510f86452a37
Source dataset
uspto-grants-2013_01
Patent number
US08361507B2

Linked notes

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