US 12,065,395 B2
Processes for the preparation of deuterated D-serine
Adam Morgan, Ashland, MA (US); and Robert S. Lewis, Lexington, MA (US)
Assigned to Sun Pharmaceutical Industries, Inc., Princeton, NJ (US)
Appl. No. 17/601,348
Filed by Sun Pharmaceutical Industries, Inc., Princeton, NJ (US)
PCT Filed Apr. 3, 2020, PCT No. PCT/US2020/026739
§ 371(c)(1), (2) Date Oct. 4, 2021,
PCT Pub. No. WO2020/206367, PCT Pub. Date Oct. 8, 2020.
Claims priority of provisional application 62/828,884, filed on Apr. 3, 2019.
Prior Publication US 2022/0169595 A1, Jun. 2, 2022
Int. Cl. C07C 227/32 (2006.01); C07D 263/04 (2006.01)
CPC C07C 227/32 (2013.01) [C07D 263/04 (2013.01)] 21 Claims
OG exemplary drawing
 
1. A method for preparing D-serine-2-d,

OG Complex Work Unit Chemistry
the method comprising:
contacting a compound of Formula E;

OG Complex Work Unit Chemistry
 wherein
R2 is C1-C6alkyl, C3-C6cycloalkyl, or aryl; and
R3 is H, D, or a protecting group,
with acid under conditions suitable for opening of the oxazolidine ring;
and optionally removing the R3 protecting group in the same or in a separate step as the contacting step,
such that D-serine-2-d is formed;
wherein the D-serine-2-d has a deuterium incorporation of at least 90% at the position specified as deuterium.