US 7,550,622 B2
Cycloalkylamidoacid compounds, processes for making and uses thereof
Isabelle Gallou, Danbury, Conn. (US); Nizar Haddad, Danbury, Conn. (US); Chris Senanayake, Brookfield, Conn. (US); Xudong Wei, Ridgefield, Conn. (US); and Jinghua Xu, Ridgefield, Conn. (US)
Assigned to Boehringer Ingelheim International GmbH, (Germany)
Filed on Aug. 12, 2004, as Appl. No. 10/916,928.
Claims priority of provisional application 60/494363, filed on Aug. 12, 2003.
Prior Publication US 2005/0085544 A1, Apr. 21, 2005
Int. Cl. C07C 69/74 (2006.01); C07C 61/04 (2006.01)
U.S. Cl. 560—123  [562/505] 11 Claims
 
1. A process

OG Complex Work Unit Drawing
comprising:
a) alkylating a cyanoester of Formula (Ia)

OG Complex Work Unit Drawing
with a base and an organic acid to make a cycloalkylcyanoester of Formula (Ib)

OG Complex Work Unit Drawing
b) performing base hydrolysis on the cycloalkyl cyanoester with a suitable base to make a cycloalkylamidoacid compound of Formula (1c);

OG Complex Work Unit Drawing
wherein R1 is 1-C4 alkyl, or H; andX=C1-2 alkylene, optionally partially or fully halogenated; and
c) treating the cycloalkylamidoacid compound of Formula (1c) with an N-brominating agent, an organic base and ROH, to make a cycloalkyl aminoester via an oxazolidinedione, as follows:

OG Complex Work Unit Drawing
wherein R=C1-10alkyl, optionally partially or fully halogenated and optionally substituted with one or more of OH, NH2,C1-6, SO2; phenyl, or CF3.