Sodium Hydroxide → Naproxen Sodium

HRID 342930Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C@H:13]([CH3:17])[C:14]([OH:16])=[O:15])[CH:7]=[CH:6]2.[OH-].[Na+:19]>>[CH3:17][C@H:13]([C:14]([O-:16])=[O:15])[C:8]1[CH:7]=[CH:6][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:12]=[CH:11][C:10]=2[CH:9]=1.[Na+:19]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 156391Naproxen

Product 1

HCID 23681059Naproxen Sodium

Procedure

It has been found that, surprisingly, when neutralizing (S)-2-(6-methoxy-2-naphthyl)propionic acid having a chiral purity below 99% with less than a stoichiometric amount of aqueous sodium hydroxide solution to form naproxen sodium, it is possible to increase the chiral purity of the naproxen sodium to 99% or more by removing the water by use of a suitable organic solvent, or simply by distilling off water from an aqueous solution.

Sources & evidence

ORD record: ord-a287f31b9303459e8fd267ab8b600b01
Source dataset: uspto-grants-1999_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05859292

Reaction notes

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