Benzilic acid → 1-(2,2-diphenyl-2-hydroxyethanoyl)-N-(2-tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)-L-prolinamide

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Reaction Steps

To a stirred solution of L-prolin-N-(2-(tert-butyloxycarbonylaminomethyl)-5-chlorobenzyl)amide (0.17 g, 0.45 mmol) in DMF (1 mL) was added benzilic acid (0.23 g, 0.51 mmol), N-methylmorpholine to pH=8 (as measured on wetted E. Merck pH indicator strips), and BOP reagent (0.31 g, 0.70 mmol). After 1 hour of mixing at room temperature, HPLC analysis indicated complete consumption of the starting amine. The mixture was filtered and purified on a preparative HPLC. Pure fractions were pooled and lyophilized to yield 1-(2,2-diphenyl-2-hydroxyethanoyl)-N-(2-tert-butyloxycarbonylaminomethyl-5-chlorobenzyl)-L-prolinamide as a solid (0.23 g, HPLC RT=3.75 min, method A; LC-MS m/z=578).

Provenance & Evidence