109774-56-3

Upstream product

• 3422-01-3 tert-butyl phenylcarbamate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 62-53-3 aniline 

Downstream Products

• 3422-01-3 tert-butyl phenylcarbamate 

Relevant academic research and scientific papers

Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols

The reaction of BOC2O in the presence and absence of DMAP was examined with some amines, alcohols, diols, amino alcohols, and aminothiols. Often, unusual products were observed depending on the ratio of reagents, reaction time, polarity of solvent, pK(a) of alcohols, or type of amine (primary or secondary). In reactions of aliphatic alcohols with BOC2O/DMAP, we isolated for the first time carbonic-carbonic anhydride intermediates; this helps explain the formation of symmetrical carbonates in addition to the O-BOC products. In the case of secondary amines, we succeeded to isolate unstable carbamic-carbonic anhydride intermediates that in the presence of DMAP led to the final N-BOC product. The effect of N-methylimidazole in place of DMAP was also examined.

A Simple Method for tert-Butoxycarbonylation of Amides

The tert-butoxycarbonyl (Boc) function was conveniently introduced onto the amide nitrogen in several secondary amides using di-tert-butyl dicarbonate in dry acetonitrile with 4-dimethylaminopyridine as catalyst.Carboxamides with different acyl groups such as formyl, acetyl and benzoyl are presented as well as derivatives of carbamic acid.Examples also include other amide types: sulfonamide, sulfenamide and phosphinamide which were all smoothly converted to the corresponding Boc derivatives under these conditions.The yields were generally excellent and the resulting Boc analogues stable compounds which could be stored for months under ordinary conditions.Some stereochemical and structural aspects of this acylation are also discussed.Bulky substituents in the proximity of the amide moiety significantly retarded the reaction and in some cases no product was detected.For one compound with an activated methine group, C acylation was observed.