P-Toluic Acid → S-atenolol toluate

HRID 1589042Notes

Reaction equation

HRID 1589042 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].C[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:25]1([CH3:1])[C:24]([C:27]([O-:29])=[O:28])=[CH:23][CH:22]=[CH:21][CH:26]=1

Participants

4

Reactant 2

HCID 7470P-Toluic AcidHCID 175540Esatenolol

Product 1

HCID 86745987S-atenolol toluate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

S-atenolol (optical purity, 91% ee, 4.43 g) and p-toluic acid (2.28 g) are dissolved in acetone (300 ml) by heating, and the mixture is allowed to stand overnight at room temperature. The precipitated crystals are separated by filtration, and the filtrate is concentrated under reduced pressure to give S-atenolol toluate having an optical purity of 98.8% ee (5.01 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-66e95db6d21447eabd593e69b0621fcd
Source dataset
uspto-grants-1993_06
Patent number
US05223646

Reaction notes

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