Hexane → 2-Amino-3'-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone

Participants

Reaction Steps

A solution of N-methyl-N-methyloxy-2-amino-5-chlorobenzamide (24.8 g) and N-tert-butoxycarbonyl-3-bromobenzylamine (22.0 g) in tetrahydrofuran (300 ml) was cooled to −78° C. To the solution was gradually added dropwise a hexane solution (1.6 mol./L)(240 ml) of n-butyl lithium. To the mixture were then added water (300 ml) and acetic acid ethyl ester (300 ml). The organic layer was washed with water, which was dried over anhydrous MgSO4, then the solvent was distilled off. To the residual oily compound was added hexane (400 ml) to cause crystallization. The crystalline product was collected by filtration to give 2-amino-3′-tert-butoxycarbonylaminomethyl-5-chlorobenzophenone (12.5 g) as pale yellow crystals.

Provenance & Evidence