P-Toluic Acid → S-atenolol p-toluate

HRID 1589043Notes

Reaction equation

HRID 1589043 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 stirred 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. stirringthe mixture is stirred at room temperature for 10 hours
  3. customThe precipitated crystals are separated by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-dddde6b0385f4496bc94de0b33051909
Source dataset
uspto-grants-1993_06
Patent number
US05223646

Reaction notes

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