[Dea]

Hello again!

I´d like to treat the indole-derivated diketopiperazine compound (see the attachment) with p-TsOH, to transform the lactim ether group into the keto group. I´m curious if p-TsOH would remove the Boc protecting group, which I´d be happy to see it happening. Thanks!

D

[AWK]

In most cases even acetic acid removes BOC protecting group

[CEDLIN]

PTsOH is a well known Boc deprotecting reagent.  It's mentioned in the tables in the back of Protecting Groups in Organic Synthesis (Greene).  So my guess is you will get the desired transformation

[Dea]

I figured so, because acid conditions remove Boc protecting group....wanted to double-check with the proffesionals here :-)
If I can nail both the transformation into ketone and Boc-removal in one shot, I've got my darn total synthesis down! :-) 

[organic help]

We have also had some good luck with weak/medium acid resins removing BOC groups too.