66851-70-5

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 22839-47-0 L-Asp-L-Phe-OMe 
• 13798-75-9 N^α-t-butoxycarbonylaspartic acid α-N-hydroxysuccinimide ester β-benzyl ester 
• 88121-96-4 Boc-Asp(Phe-NH₂)-OBzl 
• 60058-69-7 (tert-butyloxycarbonyl)-β-benzyl-L-aspartyl-L-phenylalanine amide 
• 24730-33-4 (S)-2-amino-3-phenylpropanamide hydrobromide 

Downstream Products

• 66851-71-6 L-Aspartyl-L-phenylalanine amide trifluoroacetate 

Relevant academic research and scientific papers

Process for the preparation of azacycloalkylakanoyl pseudotetrapeptides

This invention is directed to a process for preparing a pseudotetrapeptide of formula I or a salt or prodrug thereof wherein is optionally nitrogen protected azaheterocyclyl; is a single or double bond; q is 1-5; B is alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, aralkyl, alkylaryl, or alkylaralkyl; Q2 is H or a carboxylic acid protecting group; J is —H, alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, substituted aryl, aralkyl, substituted aralkyl; L is OR1, or NR1R2, where R1 and R2 are independently —H, alkyl, cycloalkyl, cycloalkylalkyl, alkylcycloalkyl, alkylcycloalkylalkyl, aryl, aralkyl, alkylaryl or alkylaralkyl; and p is 1 or 2 which comprises the coupling of two dipeptides or psuedopeptides.

Effect of Piperidine on Benzylaspartyl Peptides in Solution and in the Solid Phase

Basic conditions (e.g. piperidinolysis), used for the removal of the Nα-9-fluorenylmethyloxycarbonyl group, lead to significant cleavage of side-chain benzyl esters of peptides containing benzylaspartyl residues both in solution and solid-phase syntheses, the intermediate imide derivative is slowly transformed to a mixture of piperidides.