Triethylamine → HCID 22876691, compound

Participants

Reaction Conditions

Reaction Steps

To a -70° C. solution in THF (100 mL) of 4-[4-(4-cyanophenyl)phenoxy]butanoic acid (1.00 g, 3.66 mmol), prepared as in Example 3, was added triethylamine (0.64 mL, 4.62 mmol) and pivaloyl chloride (0.49 mL, 3.91 mmol). The reaction mixture was stirred for 15 minutes at -70° C., 45 minutes at 0° C., and then was cooled back to -70° C. In a separate flask, n-butyllithium (2.5M in hexanes, 2.56 mL, 6.40 mmol) was added via syringe to a -78° C. a solution in THF (50 mL) of (S)-(-)-4-benzyl-2-oxazolidinone. The oxazolidinone anion solution was then added to the mixed anhydride solution via cannula. The reaction mixture was then warmed slowly to ambient temperature and stirred overnight. The reaction mixture was quenched with aqueous 1M HCl and extracted with ethyl ether. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting white solid was azeotroped with ethyl ether and purified by chromatography on silica gel (2% methanol-dichloromethane) to give N-[4-(4-(4-cyanophenyl)phenoxy)butanoyl]-(S)-(-)-4-benzyl-2-oxazolidinone (1.30 g, 82%).

Provenance & Evidence