N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester → HCID 87376746, compound

Participants

Reaction Steps

A solution of 2-(piperidin-4-yl)-3-(acetylthio)propanoic acid (0.6 g, 1.72 mmol) and Boc-glycine-N-hydroxysuccinimide ester (0.52 g, 1.9 mmol) was stirred in 15 mL of dioxane for 18 hours. The reaction mixture was concentrated, partitioned between ethyl acetate and 1 M NaHSO4. The organic layer was concentrated to give 2-(1-(t-butoxycarbonylaminomethylcarbonyl)-piperidin-4-yl)-3-(acetylthio)propanoic acid, which was dissolved in 10 mL of 1:1 methylene chloride-TFA for 1 hour. The reaction mixture was then concentrated. The resulting residue was dissolved in water-methanol, cooled to 0° C. and purged with nitrogen gas. Aqueous NH4OH was added and the resulting reaction mixture was stirred for 1 hour and then concentrated to an oil. Purification by prep HPLC afforded 65 mg of 2-(1-(aminomethylcarbonyl)-piperidin-4-yl)-3-mercaptopropanoic acid; NMR (D2O) 1.2-1.21 (m, 2), 1.51-1.82 (m, 3), 2.30-2.40 (m, 1), 2.48-2.71 (m, 2), 2.90-3.00 (m, 1), 3.55 (m, 1), 3.82 (m, 2), 4.21 (m, 1) ppm.

Provenance & Evidence