Question

2) Amines are often protected with the tert-butyloxycarbonyl BOC) group. Show the mechanism of fomation of the BOC protected amine (a carbamate). Be sure to show all bonds formed broken and inclade all intermediates including the appropriate formal charge BOOO Do you expect that the carbamate functional group is more or less reactive than an amide towards nacleophilic addition? Bricfly explain your reasoning The BOC protecting group can be removed under acidic conditions, such as treatment with tnifloroacetic acid (TFA) in dichloromethane. Suggest a mechanism for the reaction below. Note: TFA is a water free acid I. TFA) Now put this information to use.... uggest a synthesis of Carmosine, a dipeptide thought to roduce the effects of aging by minimizing glycation. Hint- the methyl ester acts a protecting group for the carboxylic acid 卢

Answer 1

Na2C»3 +NH eucine 田 Amino rn fhis reacton Leucine act as a nuclko phile and group fthe amino auid protete8o Mec hanism Storg bone CO2

OH CF +Co2 + DH TFA Dichlono Solvert- + 사H Mechamism aSSume NH R-NH 田。 2 R- NH2 QNH Produet - product equivalant

Precedwu for the fomaion of. camosine: OH Na2Co3 HN 2 CH now NA DCc CB) NH dlichlono A CH NH depwteeion Camosine