[Kaladiscope]

Hi,

Do u think that is possible to make a deesterification on this linker and therefore to get the following things¿

Thanks in advance

[discodermolide]

Hi,

Do u think that is possible to make a deesterification on this linker and therefore to get the following things¿

Thanks in advance

In the example you show what is R in RNH (if you can tell me). TMSBr will react with the NH of the RNH.
You have a benzylester, the best way to deprotect it is hydrogenation over 10% Pd/C at rt and normal pressure. If for any reason it is slow increase the pressure.

[Kaladiscope]

It is an amide bond, so CO-NH. So I don't think that it will react with TMSBr. In fact what I want to avoid is the deesterification of this linker but since I have to use TMSBr to make a deesterification of other stuff in the R, I am just afraid about it.

[discodermolide]

It is an amide bond, so CO-NH. So I don't think that it will react with TMSBr. In fact what I want to avoid is the deesterification of this linker but since I have to use TMSBr to make a deesterification of other stuff in the R, I am just afraid about it.

I think you will find some de-esterification taking place, perhaps more than we might anticipate and the H in RNH will still react with TMSBr

[Babcock_Hall]

We have sometimes removed benzylesters using a related reagent TMSCl/NaI when hydrogenation was not an option.  The reaction required somewhat elevated temperatures (I think we ran it around 45 °C), but the citations on which we based our conditions gave varying values of time and temperature.  I seem to recall thinking that TMSBr would be more sluggish than TMSCl/NaI, but I don't recall my reasoning.  There is a separate thread about this deesterification reaction from roughly six months ago or so.

[discodermolide]

We have sometimes removed benzylesters using a related reagent TMSCl/NaI when hydrogenation was not an option.  The reaction required somewhat elevated temperatures (I think we ran it around 45 °C), but the citations on which we based our conditions gave varying values of time and temperature.  I seem to recall thinking that TMSBr would be more sluggish than TMSCl/NaI, but I don't recall my reasoning.  There is a separate thread about this deesterification reaction from roughly six months ago or so.

TMSCl/NaI generates TMSI in situ, the temperature is required to get it to generate!