92136-48-6

Upstream product

• 23912-50-7 N-benzoyl-phenylalanine hydrazide 
• 107-19-7 propargyl alcohol 
• 2566-22-5 DL-N-benzoylphenylalanine 

Downstream Products

• 74923-17-4 methyl N-benzoylphenylalaninate 
• 119839-43-9 2-Amino-2-benzyl-penta-3,4-dienoic acid methyl ester 
• 92136-52-2 (R,S)-allenyl-phenylalanine 
• 119839-38-2 4-Benzyl-2-phenyl-4-propa-1,2-dienyl-4H-oxazol-5-one 
• 92136-50-0 2-benzoylamino-2-benzylpenta-3,4-dienoic acid methyl ester 

Relevant academic research and scientific papers

Ceric(IV) ammonium nitrate in the selective conversion of hydrazides to esters

Hydrazides were treated with ceric(IV) ammonium nitrate (CAN) in the presence of the appropriate alcohol as a nucleophile to afford esters in good yields. Reactions took place exclusively at the hydrazino moiety even when other sensitive groups were present in either of the partners.

SYNTHESIS OF α-AMINO ACIDS WITH β,γ-UNSATURATED SIDE CHAINS

α-Amino acids with allenyl, vinyl and acetylenic side chains can be synthesized using non-enolate based strategies.The ester enolate-Claisen rearrangement applied to propargylic esters of N-protected α-amino acids is of limited utility since only poor yields of allenic product are obtained with the N-Boc glycine esters, the system which give the most reproducible results.However, α-allenyl-α-amino acids that are fully functionalized on the α-carbon are available through the agency of 4-allenyl-2-phenyloxazolones 4 ( obtained from propargyl esters of N-benzoyl protected amino acids via cyclization and Claisen rearrangement ) provided that Meerwein's reagent is used to facilitate hydrolysis of the benzamide function in 5.A variety of α-substituted glycinates, including those with α-vinyl and α-acetylenic functions, can be prepared using a two step sequence involving condensation of the cationic glycine synthon 22 with various organomagnesium reagents, followed by hydrolysis.