[zuriel]

Hi folks,

Can anyone suggest other possible reagents for cleaving this pivalate ester? Sodium hydroxide and HCl were tried but to no avail....starting material recovered. Looking for something that won't affect the other functionalities if at all possible - thanks 

[Dan]

I'd give aminolysis with ammonia a shot. There's a lot of bulk here, I can see this being tough.

[zuriel]

Thanks for the tip, Dan! Would you have a general procedure at hand for the aminolysis?

[zuriel]

Also would aminolysis not make an amide where the pivalate is?

[TheUnassuming]

Pig liver esterase.
It works great for cleaving esters when I'm estimating pk/pd of a pro-drug.  One of which was actually a piv group. 

[SDVENHI]

This looks like a tough hydrolysis.  As suggested above, aminolysis could do the job.  I would also consider hydrazine hydrate in an alcohol such as ethanol