4-Methylmorpholine → HCID 10046415, compound

Participants

Reaction Steps

For the preparation of the ester starting material, m-(1-t-butoxyformamido)benzoic acid in THF is activated (2 hours, 0° C.) with 2-chloro-4,6-dimethoxy-1,3,5-triazine and N-methylmorpholine and reacted with β-alanine benzyl ester p-toluenesulphonate and N-methylmorpholine to give N-[m-(1-t-butoxyformamido)benzoyl]-β-alanine benzyl ester, m.p. 130°-131° C. Cleavage with trifluoroacetic acid gives N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate. Nα -Z-Nω -Nitro-L-arginine is activated (4 minutes, -10° C.) with isobutyl chloroformate and triethylamine in THF and coupled with N-(m-aminobenzoyl)-β-alanine benzyl ester trifluoroacetate and triethylamine to give the desired benzyl ester, m.p. 157°-160° C.

Provenance & Evidence