P-Toluic Acid → S-atenolol toluate

HRID 654323Notes

Reaction equation

HRID 654323 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-21b2119193b54529818f19273edba555
Source dataset
uspto-grants-1992_07
Patent number
US05130482

Reaction notes

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