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Another common example is the reaction of a primary amine or secondary amine with a carboxylic acid or with a carboxylic acid derivative to form an amide. This reaction is widely used, especially in the synthesis of peptides. On the simple addition of an amine to a carboxylic acid, a salt of the organic acid and base is obtained.
Reaction mechanism for the amine formation from a carboxylic acid via Schmidt reaction. In the reaction mechanism for the Schmidt reaction of ketones, the carbonyl group is activated by protonation for nucleophilic addition by the azide, forming azidohydrin 3, which loses water in an elimination reaction to diazoiminium 5.
NHS is commonly found in organic chemistry or biochemistry where it is used as an activating reagent for carboxylic acids. [3] Activated acids (carboxylates) can react with amines to form amides for example, whereas a normal carboxylic acid would just form a salt with an amine.
Tertiary aromatic amines can be used in the Petasis reaction as another equivalent of amine nucleophile. The mechanism is similar to the N-substituted indole case. The reaction is carried out under harsh conditions (24-hr reflux in 1,4-dioxane), but the resultant carboxylic acid is obtained in reasonable yield.
HATU is commonly encountered in amine acylation reactions (i.e., amide formation). Such reactions are typically performed in two distinct reaction steps: (1) reaction of a carboxylic acid with HATU to form the OAt-active ester; then (2) addition of the nucleophile (amine) to the active ester solution to afford the acylated product.
Ugi reaction: Isocyanide, carboxylic acid, ketone, primary amine Bodroux reaction [22] [23] Carboxylic acid, Grignard reagent with an aniline derivative ArNHR' Chapman rearrangement [24] [25] Aryl imino ether: For N,N-diaryl amides. The reaction mechanism is based on a nucleophilic aromatic substitution. [26] Leuckart amide synthesis [27 ...
One plausible reaction mechanism is depicted below: [15]. Detailed Ugi mechanism. Amine 1 and ketone 2 form the imine 3 with loss of one equivalent of water. Proton exchange with carboxylic acid 4 activates the iminium ion 5 for nucleophilic addition of the isocyanide 6 with its terminal carbon atom to nitrilium ion 7.
Coupling of two amino acids in solution. The unprotected amine of one reacts with the unprotected carboxylic acid group of the other to form a peptide bond.In this example, the second reactive group (amine/acid) in each of the starting materials bears a protecting group.