US 12,421,246 B2
Method for synthesis of diazabicyclo[6.2.0]decane related compounds
Francis G. Fang, Andover, MA (US); Branko Mitasev, North Reading, MA (US); and Jiong Yang, Andover, MA (US)
Assigned to Eisai R&D Management Co., Ltd., Tokyo (JP)
Appl. No. 17/421,922
Filed by Eisai R&D Management Co., Ltd., Tokyo (JP)
PCT Filed Jan. 9, 2020, PCT No. PCT/US2020/012839
§ 371(c)(1), (2) Date Jul. 9, 2021,
PCT Pub. No. WO2020/146568, PCT Pub. Date Jul. 16, 2020.
Claims priority of provisional application 62/790,340, filed on Jan. 9, 2019.
Prior Publication US 2022/0112207 A1, Apr. 14, 2022
Int. Cl. C07D 487/04 (2006.01); C07C 229/36 (2006.01); C07C 247/10 (2006.01); C07C 311/18 (2006.01); C07D 203/12 (2006.01); C07D 205/04 (2006.01); C07D 307/33 (2006.01); C07D 317/28 (2006.01); C07D 403/06 (2006.01); C07D 405/14 (2006.01); C07D 491/147 (2006.01)
CPC C07D 491/147 (2013.01) [C07C 311/18 (2013.01); C07D 307/33 (2013.01); C07D 403/06 (2013.01); C07D 405/14 (2013.01); C07D 487/04 (2013.01)] 46 Claims
 
1. A method of forming a solid compound given by Formula I:

OG Complex Work Unit Chemistry
wherein:
R1 is —I, —Cl, —Br, or

OG Complex Work Unit Chemistry
R2 is C(O)R3;
wherein R3 is —O− and a positive counterion ionically associated with Formula I;
P1 is a nitrogen protecting group;
wherein the method comprises reacting a reactant of Formula II

OG Complex Work Unit Chemistry
with a base and resolving the racemic mixture by crystallization with a chiral reagent.