Methanesulfonic Acid → Eprosartan Mesylate

HRID 1037676

Reaction equation

HRID 1037676 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)(=O)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 176Acetic AcidSolvent2×

Procedure

After numerous trials, the inventor found that: eprosartan was suspended or dissolved in glacial acetic acid, then methanesulfonic acid was added to obtain a clear solution of eprosartan mesylate in glacial acetic acid; after about 1 hour of stirring, eprosartan mesylate solid would precipitate slowly, and thus the salification of eprosartan with methanesulfonic acid avoids embedment; ethyl acetate was added to render eprosartan mesylate crystallized completely, the obtained solid was easy to filter and drain under a reduced pressure, the wet product obtained had a low solvent content and thus was easy to dry. In addition, the new process of adding methanesulfonic acid into a solution of eprosartan in acetic acid did not produce new impurities, and the originally existing impurities decreased by some extent.

Sources & evidence

ORD record
ord-5c5c24b4904c4c7ba778109f48b42b22
Source dataset
uspto-grants-2013_10
Patent number
US08546585B2

Linked notes

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