(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide → (2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	(2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide	HCID 46946413	—
Reactant	Lithium 1-(1-acetylpiperidin-4-yl)azetidine-2-carboxylate	HCID 86692767	—
Product	(2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide	HCID 71711972	—

Reaction Steps

The reaction of (2S,4R)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 7H and lithium 1-(1-acetylpiperidin-4-yl)azetidine-2-carboxylate 20F carried out according to the general procedure L yielded (2S,4R)-1-(1-(1-acetylpiperidin-4-yl)azetidine-2-carbonyl)-4-(2-chlorophenylsulfonyl)-N-(1-cyanocyclopropyl)pyrrolidine-2-carboxamide 1:1 epimers as an off-white solid (93%). MS ISP (m/e): 526.3 (100) [(M+H)]]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08802665B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-b1edbb1baf4846d8a83334b2fdc76e26
Source note	uspto-grants-2014_08