Methanesulfonic Acid → Eprosartan Mesylate

HRID 1808665

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

Conditions

Temperature: 8 °C

Procedure

Crude eprosartan free base (50 gm, obtained in reference example 1) is stirred with isopropyl alcohol (750 ml), the reaction mass is cooled to 8° C. and then methane sulfonic acid (34 gm) is added drop wise to the mass at 0-5° C. The reaction mass is stirred for 5 hours 30 minutes at 0-5° C., the mass filtered, the material washed with isopropyl alcohol (138 ml) and then dried under vacuum at 45° C. to give 45.6 gm of crude eprosartan mesylate (HPLC purity: 98.7%).

Workup

filtrationthe mass filtered
washthe material washed with isopropyl alcohol (138 ml)
customdried under vacuum at 45° C.

Sources & evidence

ORD record: ord-e0d4db903aca4cb494c01305162df421
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08361507B2

Linked notes

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