Neutral hydrolysis reaction of acetyl 1-hydroxybenzotriazole

✍ Scribed by Kusuo Horiki

• Publisher: Elsevier Science
• Year: 1977
• Tongue: French
• Weight: 237 KB
• Volume: 18
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)83636-4

✦ Synopsis

The very recent report of the hydrolysis of acylated 1-hydroxybenzotriazole (HOW) by McCarthy et al.* prompted us to describe on our results on the hydrolysis of acetyl HOBt as our conclusions are very different. Our preceding paper reported that HOBt esters of various N-protected amino acids exist in an equilibrium of two isomers (Ia and 2a) when dissolved in dioxane and THF, and that two _acetyl isomers (l_b and 2b) can be successfully isolated. Konig and Geiger3 have reported that a: R = RIO!-NHCHCOa)N a) ' i bR 0 b: R = CH3CO-1 2 c: R=H aminolysis of these HOBt esters of N-protected amino acids proceeds very rapidly even at low temperature and to account for b) ',H 'CfN\R' O$'R this high reactivity, they postulated that the neighboring nitrogen general base catalysis shown in Fig. 1 might be responsible, without presenting any definite evidence.