methyl (2S)-1-methylpiperazine-2-carboxylate → (S)-4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-1-methylpiperazine-2-carboxylic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	methyl (2S)-1-methylpiperazine-2-carboxylate	HCID 29920832	—
Reactant	5-{(4S,5R)-4,5-Bis-(4-chloro-phenyl)-1-[4-(3-methanesulfonyl-propyl)-piperazine-1-carbonyl]-4,5-dimethyl-4,5-dihydro-1H-imidazol-2-yl}-N-tert-butyl-2-chloro-4-ethoxy-benzenesulfonamide	HCID 58894301	—
Product	(S)-4-[(4S,5R)-2-(5-tert-Butylsulfamoyl-4-chloro-2-ethoxyphenyl)-4,5-bis-(4-chlorophenyl)-4,5-dimethyl-4,5-dihydroimidazole-1-carbonyl]-1-methylpiperazine-2-carboxylic acid methyl ester	HCID 58894271	—

Reaction Steps

In a manner analogous to the method described in example 5, rac-(4S*,5R*)-2-(5-tert-butylsulfamoyl-4-chloro-2-ethoxy-phenyl)-4,5-bis-(4-chloro-phenyl)-4,5-dimethyl-4,5-dihydro-imidazole-1-carbonyl chloride (example 45) was reacted with (S)-1-methyl-piperazine-2-carboxylic acid methyl ester to give the title compound as a racemic mixture. The enantiomers were then separated by supercritical fluid chromatography (Berger Instrument Multi-Gram II, Daicel ChiralPak OD-H 3×25 cm, 35° C. at 100 bar, eluting with 25% methanol in carbon dioxide). HR-MS (ES, m/z) calculated for C37H45N5O6SCl3 [(M+H)+] 792.2151, observed 792.2148.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07851626B2
Source dataset	uspto-grants-2010_12
ORD ID	ord-6d7d5e4712244b97aa74499bbceadd2c
Source note	uspto-grants-2010_12