THE? CHEMICAL CONSTITUTION OF THE UNITS 119 



subsequent hydrolysis of the acid, whereby the phthalyl groups are 

 removed and by loss of carbon dioxide, it yields ornithine, thus : 



COOC 2 H 5 



| /Na 



Cv /COv /C0\ 



I X N/ /C 6 H 4 + Br . CH 2 . CH 2 . CH 2 . N( ) 



\cor 



COOC 2 H 5 



^UU^ 2 H 5 /< 



| /CH 2 .CH 2 .CH 2 .N( 



I 



;ooc 2 H 5 



COOC 2 H 5 /CO\ 



I /CH 2 .CH 2 .CH 2 .N/ \C 6 H 4 



cc / c \ xxx 



I \N( >C 6 H 4 



64 + 4 NaOH= 2 C 2 H 5 OH + 



/ 

 COOC 2 H 5 



COONa 



| /CH 2 .CH 2 .CH 2 .NH. CO. C 6 H 4 . COONa 4 



C< 



| \NH. CO. C 6 H 4 . COONa 



COONa 



COOH H 



| /CH 2 .CH 2 .CH Q .NH.CO.C 6 H 4 COOH | /CH, . CH a . CH 2 . NH 3 



?\NH.CO.C 6 H 4 .COOH ****** f\ NH , + 2 C 6 H 4 (COOH) 8 



COOH COOH 



An easier synthesis of ornithine was described by Fischer and 

 Zemplen in 1909. Benzoyl-S-aminovalerianic acid is prepared by the 

 oxidation of benzoylpiperidine with permanganate. This compound is 

 converted by the action of bromine and phosphorus into benzoyl-S- 

 amino-a-bromovalerianic acid, which, on treatment with ammonia, gives 

 monobenzoylornithine. The inactive ornithuric acid (dibenzoyl-a, B- 

 diaminovalerianic acid) is then easily made by benzoylation : 



C 6 H 5 . CO NH . CH 2 . CH 2 . CH 2 . CH 2 . COOH 

 C 6 H 6 . CO NH . CH 2 . CH 2 . CH 2 . CHBr . COOH 

 C 6 H 6 . CO NH . CH 2 . CH 2 . CH 2 . CH(NH 2 ) . COOH 

 C 6 H 5 CO NH . CH 2 . CH 2 . CH 2 . CH(NH OC . C 6 H 6 ) . COOH 



