Methanesulfonic Acid → Eprosartan Mesylate

HRID 1808669

Reaction equation

HRID 1808669 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]>CC(C)=O>[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 MesylateYield 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
2.5 °C

Procedure

Eprosartan free base (8 gm, obtained in example 3) is suspended in acetone (120 ml) at 25-30° C., the suspension is cooled to 0-5° C., methanesulfonic acid (5.4 gm) is added drop wise while maintaining the temperature at 0-5° C. The temperature of the mass is raised to 25-30° C. and stirred for 5 hours. The mass is cooled to 0-5° C., stirred for 1 hour, the material is filtered and then suck dried. To the resulting wet cake is added acetone (16 ml) and stirred for 15 minutes at 25-30° C. The material is filtered, washed with acetone (8 ml) and then dried to give 9 gm of pure eprosartan mesylate [HPLC Purity: 99.96%; Specific Surface Area: 1.11 m2/g; Mean particle size (D50): 11.23 μm and 90 volume-% of the particles (D90): 30.42 μm].

Workup

  1. temperaturewhile maintaining the temperature at 0-5° C
  2. temperatureThe temperature of the mass is raised to 25-30° C.
  3. temperatureThe mass is cooled to 0-5° C.
  4. stirringstirred for 1 hour
  5. filtrationthe material is filtered
  6. customsuck dried
  7. additionTo the resulting wet cake is added acetone (16 ml)
  8. stirringstirred for 15 minutes at 25-30° C
  9. filtrationThe material is filtered
  10. washwashed with acetone (8 ml)
  11. customdried

Sources & evidence

ORD record
ord-a1e9f9db88014c8d80d9196bfae79ba5
Source dataset
uspto-grants-2013_01
Patent number
US08361507B2

Linked notes

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