Diisopropylethylamine → ((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-n-[(1S)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]carboxamide

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	HOAt	HCID 181649	—
Reactant	N-(tert-Butoxycarbonyl)-4-chloro-L-phenylalanine	HCID 2734499	—
Reactant	N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide methyliodide	HCID 10236463	—
Reactant	N-(2-(Piperazin-1-yl)phenyl)methanesulfonamide hydrochloride	HCID 21283546	—
Solvent	Dimethylformamide	HCID 6228	—
Product	((3s)(3-1,2,3,4-tetrahydroisoquinolyl))-n-[(1S)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl]carboxamide	HCID 10145280	117.9%
Product	n-[(1S)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)-2-oxoethyl](tert-butoxy)carboxamide	HCID 21060096	—

Reaction Steps

N-[(1S)-1-[(4-Chlorophenyl)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 (913 mg, 3.13 mmol), N-Boc-4-chloro-L-phenylalanine (960 mg, 3.2 mmol) (Bachem), DIEA (550 μl, 3.16 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide methiodide (1.9 g, 6.5 mmol), HOAT (440 mg, 3.2 mmol) and DMF (30 mL). The crude was purified by flash chromatography (SiO2, 1:1 hexane:EtOAc) to afford the desired compound (1.1 g). MS (ESI, pos. ion) m/z: 537 (M+H), (ESI, neg. ion) m/z: 535 (M−H). Calc'd for C25H33ClN4O5S: 536.19.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07115607B2
Source dataset	uspto-grants-2006_10
ORD ID	ord-4c63a4da04984bd6ad418a750660bd0d
Source note	uspto-grants-2006_10