Ammonia → N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	2-Phenylpyrrolidine	HCID 261892	—
Reactant	3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N-(2,2,2-trifluoro-1-phenylethyl)benzamide	HCID 11490238	—
Reactant	3-({2-[(Tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid	HCID 58856337	—
Solvent	Methanol	HCID 887	—
Product	N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide	HCID 11215160	—

Reaction Steps

N-{3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(2-phenylpyrrolidin-1-yl)carbonyl]phenyl}-N-propylmethanesulfonamide was prepared from 3-({2-[(tert-butoxycarbonyl)amino]-2-methyl-3-phenylpropoxy}methyl)-5-[(methylsulfonyl)(propyl)amino]benzoic acid (intermediate XI) and 2-phenylpyrrolidine following a similar procedure as described for the preparation of 3-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-5-[(methylsulfonyl)(propyl)amino]-N-(2,2,2-trifluoro-1-phenylethyl)benzamide with additional purification by ion exchange chromatography (Varian Bond Elut SCX, eluting with MeOH followed by 2.0M.NH3 in MeOH). HRMS (ES, M+H) calculated for C32H41N3O4S: 564.2891, found: 564.2891.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07354942B2
Source dataset	uspto-grants-2008_04
ORD ID	ord-69f4b1af1ba24bd0820944565f014999
Source note	uspto-grants-2008_04