β-Amino acids

Summary

• 1. It has been established that by the decarboxylation of the glycidic acid

  

  , obtained by Darzens' method from cis-decahydro-2-naphthol of m.p. 105°, a mixture of stereoisomeric decahydro-2-naphthaldehydes is formed; these have not been investigated further.

• 2. The synthesis has been affected, by Rodionov's method, of β-(2-decalyl)-β-alanine (β-aminodecahydro-2-naphthalenepropionic acid), which also appeared to be a mixture of isomers, the separation of which was not carried out.

• 3. By taking advantage of the different ether-solubilities of the acid chlorides of the N-benzoylated β-(2-decalyl)-β-alanines, the corresponding amides, m.p. 210–212° and 250–252°, were isolated.

• 4. The two amides were converted by careful hydrolysis into the isomeric N-benzoylated β-(2-decalyl)-β-alanines.

• 5. It has been shown that when the amide of N-benzoyl-β-(2-decalyl)-β-alanine is heated with acetic anhydride, a transacylation reaction occurs, and instead of 6-(2-decalyl)-6,6-dihydro-2-phenyl-4(3H)-pyrimidinone the corresponding 2-methyl derivative is obtained.

• 6. In order to characterize β-(2-decaclyl)-β-alanine, the corresponding ureido acid and 6-(2-decalyl)-hydrouracil were prepared.

• 7. Esters and hydrazides of N-benzoyl-β-(2-decalyl)-β-alanine have been prepared, and, by means of the Curtius reaction, they have been converted into 3-benzoyl-4-(2-decalyl)-2-imidazolidones and the corresponding 4-(2-decalyl)-2-imidazolidinone.