N-Benzylphenethylamine → 9-(Benzyl-phenethyl-amino)-nonanoic acid

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Reaction Steps

The title compound, m/e=406.6 ([M+H]+), was produced in analogy with example 64, steps 1 to 4. Thus, 9-oxononanoic acid methyl ester was reacted in step 1 with N-benzyl-2-phenylethylamine, leading to 9-(benzyl-phenethyl-amino)-nonanoic acid methyl ester, which was hydrolyzed in step 2 to afford 9-(benzyl-phenethyl-amino)-nonanoic acid. This was coupled in step 3 with (R)-3-amino-4-dimethylamino-butyric acid benzyl ester dihydrochloride, leading to (R)-3-[9-(benzyl-phenethyl-amino)-nonanoylamino]-4-dimethylamino-butyric acid benzyl ester, which was hydrogenated in step 4.

Provenance & Evidence