US 7,589,221 B2
Process for producing (2R)-2-propyloctanoic acid and intermediate therefor
Yasumasa Hamada, Chiba (Japan); Tomoyuki Hasegawa, Sakai-gun (Japan); Toshiaki Matsui, Sakai-gun (Japan); and Eiji Kasamatsu, Sakai-gun (Japan)
Assigned to Ono Pharmaceutical Co., Ltd., Osaka (Japan)
Appl. No. 10/560,176
PCT Filed Jun. 09, 2004, PCT No. PCT/JP2004/008387
§ 371(c)(1), (2), (4) Date Dec. 09, 2005,
PCT Pub. No. WO2004/110972, PCT Pub. Date Dec. 23, 2004.
Claims priority of application No. 2003-164485 (JP), filed on Jun. 10, 2003.
Prior Publication US 2006/0135802 A1, Jun. 22, 2006
Int. Cl. C07B 53/00 (2006.01); C07C 231/00 (2006.01); C07C 227/00 (2006.01)
U.S. Cl. 554—114  [564/130; 562/606] 3 Claims
 
1. A process for producing (2R)-2-propyloctanoic acid, which comprises:
subjecting (2R)-2-hexyloxirane to a two-carbon adding reaction with ring-opening reaction, followed by a reaction to protect the hydroxyl group with a removable protective group by reacting the hydroxyl group with a sulfonyl chloride, a phosphoryl chloride or an acid anhydride to obtain a compound represented by formula (I):

OG Complex Work Unit Drawing
wherein X represents a hydroxyl group which is protected by a removable protective group, and then
subjecting the compound to a one-carbon adding reaction to obtain (2R)-2-propyloctanamide, followed by recrystallization and hydrolysis.