Naproxen (process): spot the resolution conditions flaw

Single question

Penultimate step of the Syntex naproxen process: resolve racemic 2-(6-methoxy-2-naphthyl)propanoic acid by salt crystallization with a chiral base. The atoms and product are right. Check the base.

Classical resolution requires a chiral resolving agent

Syntex naproxen cinchonidine resolution

Achiral bases give racemic salts

Find the flaw

Click the step that contains the flaw, or pick “No flaw” if you think every step is correct.

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