Acetic Acid → Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-hydroxy-1,6-naphthyridine-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-(5-(tert-butoxycarbonylamino)-N-methylpentylsulfonamido)-8-(tosyloxy)-1,6-naphthyridine-7-carboxylate (Example 2.1; 8.68 mmol) was dissolved in DMF (17 ml) at 40° C. and transferred to a 33% solution of NaOMe in MeOH (4.1 ml; 21.7 mmol) over 1-2 min at 25° C. The resulting yellow homogenous mixture was heated to 50° C. Mixture was cooled to 25° C. over 15 min and aged at 25° C. for 15 min. Acetic acid (1 ml) was added over 1 min, then water was added. The slurry was aged for 30 min and filtered. The filter cake was washed with water, and dried to give the target compound in 61% yield.

Provenance & Evidence