[faust]

Hello,

I have this kind of molecule : EtOOC-R-NH-allyl (1)

I have to put an electronwithdrawing group on my amine (I don't have to unprotect my amine after). And this group couldn't contain aromatic or fluorine.

So may be I can try with a carbamate.

Like reacting (1) with Cl-COOMe.

But after I have to hydrolyse my ester. So can I hydrolyse my ester group without touching my carbamate?

Like this :  EtOOC-R-N(COOMe)-allyl ---> HOOC-R-N(COOMe)-allyl

Because I'm afraid about making a carbamic acid with will decarboxylate...

Another solution is to use boc, but can I selectively hydrolyze COOEt without touching COO-tBu?

Thank you

Fajan

[movies]

BOC groups are pretty stable towards base, so you might be able to  pull that off.  Typically, BOC groups are removed under acidic conditions, not basic.

Another amine group might be another allyl group or a Fmoc group, those should be base stable as well.

Another option is to use a methyl or t-butyl ester and that opens up some other ester cleavage options.