P-Toluic Acid → S-atenolol p-toluate

HRID 654324Notes

Reaction equation

HRID 654324 reaction equation
[CH3:1][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:3].[CH3:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]([OH:29])=[O:28])=[CH:25][CH:26]=1>CC(C)=O>[CH3:3][CH:2]([NH:4][CH2:5][C@H:6]([OH:19])[CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][C:16]([NH2:18])=[O:17])=[CH:13][CH:14]=1)[CH3:1].[C:21]1([CH3:20])[CH:26]=[CH:25][C:24]([C:27]([O-:29])=[O:28])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 7470P-Toluic AcidHCID 175540Esatenolol

Product 1

HCID 86745988S-atenolol p-toluate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The S-atenolol having an optical purity of 96.5% ee (10.77 g) thus obtained and p-toluic acid (5.54 g) are dissolved in acetone (1 liter) by heating with stirring and the mixture is sitrred at room temperature for 10 hours. The precipitated crystals are separated by filtration and the filtrate is concentrated under reduced pressure to give S-atenolol p-toluate having an optical purity of 98.5% ee (14.47 g).

Workup

  1. temperatureby heating
  2. customThe precipitated crystals are separated by filtration
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-9e2397ba25744b9a840cb98c86490384
Source dataset
uspto-grants-1992_07
Patent number
US05130482

Reaction notes

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