Amide nitrogen

You should be able to identify the product by ascertaining which of the two nitrogens (amide or amine) is the more nucleophilic. 

By analogy to N- and O-dealkylation reactions, one might expect esters and amides to be susceptible to P450-catalyzed oxidative attack at the a-carbon to oxygen (esters) or a to nitrogen (amides). This is indeed the case and was first established (132) by demonstration that the pyridine diester (Fig. 4.66) was oxidatively cleaved by rat-liver microsomes to yield the monoacid as shown. 

The nitrogen that reacts is the one that is a tertiary alkylamine. Of the other two nitrogens, is attached to an aromatic ring and is much less basic and less nucleophilic. The third nitrogen, , is an amide nitrogen amides are less nucleophilic than amines. 

Compound Solvent Screening constants Amine-ammonium nitrogen Amide nitrogen Notes... 

A large variety of macrolides have been isolated from natural sources. Macrolides have various ring sizes up to 62 and exhibit various characters spiroacetal-fused macrolides, polyene macrolides, macropolylides, and macrolides containing amino nitrogen, amide nitrogen, oxazole rings, or thiazole rings in their skeletons. 

Ans. Tertiary amines have no hydrogen attached to nitrogen. Amidation requires the presence of a hydrogen on the nitrogen. There must be a hydrogen lost from the nitrogen to couple with the OH that is to be lost from the carboxylic acid. 

PEI extinguishes Immediately after removal from flame slightly yellowish, foams burnt horn nitrogen (amides, imides)... 

Amides are very different because of the delocalization of the lone pair into the carbonyl group. This makes amides more acidic but less basic and protonation occurs on oxygen rather than nitrogen. Amides have pK values of around 15 when they act as acids, making them some IQi times more acidic than amines. The pK of protonated amides is around 0, making them some 10i° times weaker as bases. 

Phosphoribosyl glycineamide synthetase Carbon-nitrogen Amide synthesis Yes Yes... 

The amounts of total nitrogen, amino nitrogen, amide nitrogen, ammonia nitrogen, and other nitrogen fractions are given in Tables XIX, XX, XXI, XXII, and XXIII. 

Hydroxamate Test for Amides. Unsubstituted (on nitrogen) amides, and the majority of substituted amides, will give a positive hydroxamate test ... 

The combination of a secondary benzyl alcohol with Hf(OTf)4 in nitromethane was a highly effective secondary benzylation system. Secondary benzylation of carbon (aromatic compounds, olefins, an enol acetate), nitrogen (amide derivatives), and oxygen (alcohols) nucleophiles was carried out with a secondary benzyl alcohol and 1 mol % of Hf(OTf)4 in the presence of water. Secondary benzyl alcohols and nucleophiles bearing acid-sensitive functional groups (e.g.,icri-butyldimethylsilyloxy and acetoxy groups and methyl/benzyl esters) could be used for alkylation. Hf(OTf)4 was the most active catalyst for this alkylation, and trifluoromethanesulfonic acid (triflic acid, HOTf) also proved to be a good catalyst. In such cases, the catal)fiic activity of metal triflates and HOTf increased in the order La(OTf)3 [Pg.346]

The donors (H atoms) are amine, amide, and hydroxyl hydrogens, and acceptors (X atoms) are uncharged ring nitrogens, amide nitrogens, or hydroxyl, ester carbonyl, or carboxylic acid oxygens. 

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