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t-Butoxycarbonylaminovaleric acid 5-Aminovaleric acid was converted under Schotten-Baumann conditions with di-t-butyl carbonate in the usual manner into the corresponding N-protected acid, melting point 48-50 (from ether/hexane).
With potassium carbonate; In hydrogenchloride; water;
E. 5-guanidinopentanoic acid was prepared by the method of Miller, et al., Synthesis, 777 (1986), which is incorporated herein by reference. 2.00 g of 5-aminovaleric acid was dissolved in a solution of 2.35 g of potassium carbonate in 20 ml of water followed by the portionwise addition of 2.13 g <strong>[1184-90-3]aminoiminomethanesulfonic acid</strong> over 10 minutes. The solid which formed after stirring at room temperature overnight was collected and recrystallized from water. The guanidine was dissolved in dilute hydrochloric acid solution and the solution evaporated in vacuo. The residue was washed with 2-propanol which was then evaporated to give 5-guanidinopentanoic acid hydrochloride.
A mixture of 4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.34 mmol) and 5-amino-valeric acid (597 mg, 5.1 mmol) in 0.5 N NaOMe in MeOH solution (6.8 mL, 3.4 mmol) was heated to reflux overnight. Reaction mixture was diluted with water (100 mL) and acidified by 1 N HC1 solution to pH = 3-4. Precipitate was collected and rinsed with water. It was dried in vacuo to provide the title compound (102 mg, 0.27mmol) in 80% yield. LC-MS ESI-: 379.07 (M-l)
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