Chlorotrimethylsilane → (S)-1-(10,11-dihydro-5H-dibenz [b,f]azepine-5-carbonyl)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid

Participants

Reaction Steps

Following the procedure of Example 16, Step B, 811 mg (2.5 mmole) of (S)-4-(benzyloxycarbonyl)-piperazine-2-carboxylic acid (from Example 7, Step A) 680 mg (6.26 mmole) of chlorotrimethylsilane, 1.23 g (9.5 mmole) of N,N-diisopropylethylamine and 665 mg (2.5 mmole ) of 97% of 10,11-dihydro-5H-dibenz[b,f]-azepine -5-carbonyl chloride, gave 284 mg (24%) of (S)-1-(10,11-dihydro-5H-dibenz[b,f]azepine5-carbonyl)-4-(benzyloxycarbonyl)piperazine-2-carboxylic acid, mp 185° C. (softened >90° C.); TLC Rf 0.68 (Analtech SGF plates developed with isoamyl alcohol:acetone:water [5:2:1]).

Provenance & Evidence