3-Aminopropanoic acid lactam

IUPAC name 3-aminopropanoic acid lactam common name /3-propiolactam... 

Amino acids capable of forming lactams give low yields of (trifluoromethyl)amines. Thus, 4-aminobutanoic acid gives 4.4,4-trifluorobutylamine (14b) in only 7% yield, while 3,3,3-tri-fluoropropylaminc (14a) is formed from 3-aminopropanoic acid in 41 % yield.113... 

Just as amines react with esters to form amides, lactones react with amines to give lactams or are opened to give amino acid derivatives directly. When P-propiolactone (2.20) reacted with ammonia, for example, 3-aniinopropanamide (2.2Ia) was obtained. 2 Similar reaction with methylamine gaveno2.2/h but rather a 97% yield of 3-aminopropanoic acid, 2.22. Dimethylamine, however, converted 2.20 to 2.2Ic in 79% yield, along with 13% of 2.22.12... 

As just discussed in section 2.3, hydrolysis of lactams is a convenient source of amino acids. -Lactams (2-azetidinone derivatives) are a very interesting class of compounds and hydrolysis leads to 3-aminopropanoic acid derivatives ( -alanine derivatives). There are specialized methods that lead to -lactams and for this reason they have been segregated into a separate section. 

Using an identical approach, reaction of p-chlorostyrene and CSI gave the lactam, and removal of the sulfonyl group and hydrolysis with HCl gave 3-(p-chlorophenyl)-3-aminopropanoic acid. ... 

A ketene intermediate is not required in order to generate the P-lactam. In the case of 2.111, ketene formation is not possible. Reaction of the acid chloride with the imine, however, generates an intermediate where the nitrogen can displace the bromine moiety to give the lactam. The reaction of 2.111 and 2.115 proceeded, in the presence of pyridine, to give 2.772.55 Reaction with HCl gave 2,2-diethyl-3-aminopropanoic acid, 2.113. Similarly, 2,2-dipropyl and 2,2-dibutyl-3-aminopro-panoic acids were prepared from the appropriate acid chloride and 2.110. ... 

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