1-Chloro-4-acetoxynonane → 7-[1-(4(R)-hydroxy-2-nonynyl)ureido]heptanoic acid

Participants

Reaction Steps

The synthesis of this compound is carried out as described in Example 1 except that, in Step a, the 1-chloro-4-acetoxynonane is replaced by an equimolar amount of 1-bromo-4(S)-acetoxy-2-nonyne (Example K). The product of Step A is thus ethyl 7-[N-(4(S)-acetoxy-2-nonynyl)cyanamido]heptanoate. The subsequent steps yield 7-[N-(4(S)-hydroxy-2-nonynyl)-cyanamido]heptanoic acid (B) and 7-[1-(4(S)-hydroxy-2-nonynyl)ureido]heptanoic acid (C). The product of Step C is hydrogenated over a platinum on charcoal catalyst to afford 7-[1-(4(S)-hydroxy-nonyl)ureido]heptanoic acid.

Provenance & Evidence