2,3-Dihydroxybutanedioic Acid → Tartrate

HRID 1761249Notes

Reaction equation

HRID 1761249 reaction equation
[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].[C:29]([OH:38])(=[O:37])[CH:30]([CH:32]([C:34]([OH:36])=[O:35])[OH:33])[OH:31]>CS(C)=O>[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:29]([O-:38])(=[O:37])[C@@H:30]([C@H:32]([C:34]([O-:36])=[O:35])[OH:33])[OH:31]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 2162Amlodipine

Product 2

HCID 119400TartrateHCID 9801597(+)-Amlodipine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a stirred solution of 100 gm (0.245 moles) of RS amlodipine in 150 ml DMSO was added a solution of 9.2 gm (0.06 moles, 0.25 eq) of L (+) tartaric acid in 100 ml DMSO. The solid starts separating from clear solution within 5-10 mins. This was stirred for 3 hrs and solid was filtered off, washed with acetone and dried to give 58.6 gm (40.5%) R (+) amlodipine hemi L(+) tartarate mono DMSO solvate. mp. 160-162° C., 96.8% d.e. by chiral HPLC.

Workup

  1. customThe solid starts separating from clear solution within 5-10 mins
  2. filtrationsolid was filtered off
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-a584771b23714f659811db85d277a6e4
Source dataset
uspto-grants-2005_01
Patent number
US06846932B1

Reaction notes

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