Hydrochloric Acid → 5-Bromonaproxen, (S)-

HRID 1193713Notes

Reaction equation

HRID 1193713 reaction equation
O[C@H]([C@H]([C:10](=[O:26])[CH:11]([C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[C:18]([O:24][CH3:25])[C:19]=2[Br:23])[CH:14]=1)[CH3:12])C(O)=O)C(O)=O.Cl.[O:28]1CCOCC1>>[Br:23][C:19]1[C:18]([O:24][CH3:25])=[CH:17][CH:16]=[C:15]2[C:20]=1[CH:21]=[CH:22][C:13]([C@H:11]([CH3:12])[C:10]([OH:26])=[O:28])=[CH:14]2

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 543592902(R)-hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid

Product 1

HCID 115296645-Bromonaproxen, (S)-

Conditions

Temperature
90 °C

Procedure

A mixture of pure 2(R)-hydroxy-3(R)-[2-(5-bromo-6-methoxy-2-naphthyl)propanoyl]-butanedioic acid (0.441 g, 1 mmol), 1,4-dioxane (8 ml), and of conc. HCl (8 ml) was heated, under stirring, at 90° C. for 2 hours. The reaction mixture was worked up as described in example 52, to give pure 2(S)-(5-bromo-6-methoxy-2-naphthyl)-propionic acid in 98% enantiomeric excess, determined by HPLC and by 1H-NMR carried out as described in example 57.

Sources & evidence

ORD record
ord-c37d3bb7159b44aaad4d5a333e06f58b
Source dataset
uspto-grants-1989_03
Patent number
US04810819

Reaction notes

Loading…