US 6,982,344 B2
Process for preparation of optically active sulfonamides and intermediates for their synthesis
Tomomi Ikemoto, Takarazuka (Japan); Atsuko Nishiguchi, Itami (Japan); and Kiminori Tomimatsu, Minoo (Japan)
Assigned to Takeda Pharmaceutical Company Limited, Osaka (Japan)
Appl. No. 10/399,165
PCT Filed Oct. 17, 2001, PCT No. PCT/JP01/09120
§ 371(c)(1), (2), (4) Date Apr. 11, 2003,
PCT Pub. No. WO02/32859, PCT Pub. Date Apr. 25, 2002.
Claims priority of application No. 2000-323309 (JP), filed on Oct. 18, 2000.
Prior Publication US 2004/0049041 A1, Mar. 11, 2004
Int. Cl. C07C 311/51 (2006.01); C07C 311/14 (2006.01); C07C 311/28 (2006.01); C07C 303/40 (2006.01); C07B 57/00 (2006.01)
U.S. Cl. 560—12 30 Claims
 
1. A method comprising
reacting a racemate represented by the formula
R1—SO2—NH—R2  (II)
 wherein
R1 and R2 are the same or different and each is an optionally substituted hydrocarbon group or an optionally substituted heterocyclic group, and only one of R1 and R2 contains one asymmetric carbon,
or a salt thereof
with an optically active compound represented by the formula
Ra—COOH  (III)
 wherein
Ra is an optically active and optionally substituted hydrocarbon group or an optically active and optionally substituted heterocyclic group, a salt thereof or a reactive derivative thereof
to give a diastereomeric mixture represented by the formula
OG Complex Work Unit Drawing
 wherein each symbol is as defined above,
or a salt thereof, and
resolving the diastereomeric mixture or a salt thereof
wherein resolution is carried out by solvent extraction, liquid exchange, phase transfer, salting out, crystallization, recrystallization or chromatography,
to produce the diastereomer having a steric configuration of the asymmetric carbon for R1 or R2 of an R configuration or an S configuration,
or a salt thereof.