[Daedalus]

Hello all and Merry Christmas everyone for 2013!

I am a ChE/Chemistry grad. student as I was wondering if anyone know whether any protecting groups exist to convert a primary amine to a secondary amine (-NH2 to -NHR) where the secondary amine is protected against electrophiles (i.e. Acid Chloride). After an extensive literature search, I could only find phthalamide and 2,3-dimethyl pyrole diprotecting groups are resistant to attack from by acid chlorides. I was hoping to find a 2⁰ amine protecting group so I could more easily protect. deprotect the amine functionality before/after I clicked this smaller molecule onto the larger acid chloride molecule

Your help would be enormously appreciated.

Kind regards,

Ryan.

[kriggy]

can you be more specific please? Like show a sheme?
You could use some protective groups like tosyl and then alkylate?

[Daedalus]

can you be more specific please? Like show a sheme?
You could use some protective groups like tosyl and then alkylate?

Certainly.

Please refer below:

[Archer]

what exactly are you interested in? look up functional group transformations of amines and there will be a whole bunch which are unreactive towards acid chlorides.

Please give some detail as to why you want to do this.

[Daedalus]

what exactly are you interested in? look up functional group transformations of amines and there will be a whole bunch which are unreactive towards acid chlorides.

Please give some detail as to why you want to do this.

Sure, let me elaborate.

The reason that I want to do the reaction this way is so I can achieve a protection of an amine to prevent it from reacting from an acid chloride as simply and quickly as possible. The synthesis method of the diprotection (thylaminde or the dimethyl pryrole) require either perverse reaction/deprotection conditions. My reasoning for using a (mono) or a primary amine was that its is more facile to achieve and as well as deprotect.

I suppose to be more specific, would you know if a secondary protected (e.g. Boc, Fmoc, Benzylideneamine  Triphenylmethylamine, t-Butyl carbamat or any other acid/base labile N^α terminus protecting group) is resistant to any subsequent reaction with an acid chloride?

Thanks!

[Archer]

T-BOC will probably suit your purposes then.