Benzenesulfonic Acid → Amlodipine besylate

HRID 1761252Notes

Reaction equation

HRID 1761252 reaction equation
[CH3:1][CH2:2][O:3][C:4]([C:6]1[C@H:11]([C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].C([O-])(=O)C(C(C([O-])=O)O)O.[C:39]1([S:45]([OH:48])(=[O:47])=[O:46])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(O)(C)C.O>[CH3:1][CH2:2][O:3][C:4]([C:6]1[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=2[Cl:18])[C:10]([C:19]([O:21][CH3:22])=[O:20])=[C:9]([CH3:23])[NH:8][C:7]=1[CH2:24][O:25][CH2:26][CH2:27][NH2:28])=[O:5].[CH:42]1[CH:41]=[CH:40][C:39]([S:45]([OH:48])(=[O:47])=[O:46])=[CH:44][CH:43]=1

Participants

6

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 38061142,3-DihydroxybutanedioateHCID 9801597(+)-Amlodipine

Product 1

HCID 60496Amlodipine besylateYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

68.8 gm (0.122 mole, 95.2% de) R (+) Amlodipine hemi L (+) tartarate mono DMSO solvate prepared as per example 1 was suspended in aqueous isopropanol (90 ml IPA: 250 ml distilled water) and a solution of benzene sulfonic acid (19.35 gm of 90% technical grade, 0.110 mole) in 150 ml water was added. The reaction mixture was stirred for 2 hrs and the slurry was filtered, washed with distilled water, hexane, the solid was dried under vac. at 40° C. till constant weight to give R(+) amlodipine besylate (51.6 gm, 69.4% yield) 99.3 ee by chiral HPLC.

Workup

  1. filtrationthe slurry was filtered
  2. washwashed with distilled water, hexane
  3. customthe solid was dried under vac

Sources & evidence

ORD record
ord-4f76eb6a9cf746168f2a2b75f2729499
Source dataset
uspto-grants-2005_01
Patent number
US06846932B1

Reaction notes

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