Synthesis of ( 2S, 4S)-4-phenylamino-5-oxoproline derivatives.
The paper describes the synthesis of ( 2S, 4S)-4-(N-Ts)- and ( 2S, 4S)-4-(N-Boc)-phenylamino-5-oxoprolines (pyroglutamic acid). These derivatives have been shown to be useful for synthesis of their amides and peptides in spite of steric hindrances caused by bulky groups adjacent to the reaction centre. Under the conditions applied no lactam ring opening and no loss of stereochemical integrity of any of the chiral centres were observed, which has been confirmed by NMR techniques.
Nizova
I A
IA
Institute of Organic Synthesis, Ural Division of Russian Academy of Sciences, Ekaterinburg, Russia.
Krasnov
V P
VP
Levit
G L
GL
Kodess
M I
MI
D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011761:Pyrrolidonecarboxylic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011761:Pyrrolidonecarboxylic Acid