Sodium Hydroxide → sodium [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate

Participants

Reaction Steps

To a solution of a mixture (400 mg) of ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-1-cyclopenten-1-yl}methyl]-phenoxy]acetate and ethyl [3-[{2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl}methyl]phenoxy]acetate in a mixture of ethanol (10 ml) and ethyl acetate (10 ml) was added 10% palladium on carbon (50 mg). After being stirred for 6 hours under hydrogen atmosphere, the reaction mixture was filtered. The solvent was evaporated in vacuo to give a residue containing a mixture of ethyl [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate and ethyl [3-[{(1RS,2SR)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate. The residue was dissolved in ethanol (20 ml), and 1N-sodium hydroxide solution (0.80 ml) was added. After being stirred for 8 hours, the solvent was evaporated in vacuo. The residue was triturated in ether to give a mixture (350 mg) of sodium [3-[{(1RS,2RS)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate and sodium [3-[{(1RS,2SR)-2-(4,5-diphenyloxazol-2-yl)cyclopentan-1-yl}methyl]phenoxy]acetate.

Provenance & Evidence