Preparation and improved stability of N-Boc-alpha-amino-5-acyl Meldrum's acids, a versatile class of building blocks for combinatorial chemistry.
The preparation of novel N-Boc-alpha-amino-5-acyl Meldrum's acids is described. The synthetic inaccessibility and instability of several of these products have led to the development of a protocol that allows the synthesis of their corresponding 4-(dimethylamino)pyridine (DMAP) salts (5-AMA-DMAP's), which exhibit superior stability compared to that of the free 5-AMA. A simple and expedient ion-exchange method was developed for the quantitative removal of DMAP to liberate the synthetically useful DMAP-free form when needed.
Raillard
Stephen P
SP
Affymax, Inc., 4001 Miranda Avenue, Palo Alto, CA 94304, USA.
Chen
Weiwei
W
Sullivan
Edward
E
Bajjalieh
William
W
Bhandari
Ashok
A
Baer
Ted A
TA