1,2-Dichloroethane → n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	3,4-Dichloro-N-((1,1-dimethylethoxy)carbonyl)-D-phenylalanine	HCID 7015811	—
Reactant	N-(2-(Piperazin-1-yl)phenyl)methanesulfonamide hydrochloride	HCID 21283546	—
Solvent	Dimethylformamide	HCID 6228	—
Product	n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-carboxamide	HCID 10282776	113.3%
Product	n-[(1r)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide	HCID 21060073	—

Reaction Steps

N-[(1R)-1-[(3,4-Dichlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide was prepared according to the procedure for Preparation XIX using (methylsulfonyl)(2-piperazinylphenyl)amine hydrochloride (800 mg, 2.8 mmol), N-Boc-D-3,4-dichlorophenylalanine (930 mg, 2.80 mmol) (Peptech), DIEA (480 μl, 2.80 mmol), EDC (1.66 g, 5.60 mmol), HOAT (400 mg, 3.0 mmol) and DMF (10 mL). The crude product was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc) and concentrated in vacuo to afford the desired compound (1.0 g). MS (ESI, pos. ion) m/z: 571 (M+H), (ESI, neg. ion) m/z: 569 (M−H). Calc'd for C25H32Cl2N4O5S: 570.15.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115607B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-c7d3d40ed73745b5a345fbf909da5db3
Source note	uspto-grants-2006_10