1,2-Dichloroethane → 2-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dichloroethane	HCID 11	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,2,3,4-Tetrahydro-7-nitroisoquinoline	HCID 6424833	—
Reactant	(3R)-3-(((tert-butoxy)carbonyl)amino)-4-(2-fluorophenyl)butanoic acid	HCID 7021570	—
Product	2-[(3R)-3-[(tert-Butoxycarbonyl)amino]-4-(2-fluorophenyl)butanoyl]-7-nitro-1,2,3,4-tetrahydroisoquinoline	HCID 69222742	—

Reaction Steps

(3R)-3-[(tert-Butoxycarbonyl)amino]4-(2-fluorophenyl)butanoic acid (0.69 g; 2.34 mmol) and 7-nitro-1,2,3,4 tetrahydroisoquinoline (0.50 g; 2.34 mmol) were treated with EDC (0.54 g, 2.8 mmol), HOBt (0.38 g, 2.8 mmol) and N,N-diisopropylethylamine (0.60 g, 4.67 mmol) essentially following the procedure outlined in Example 1, Step A. Purification by flash chromatography (silica gel; 35% ethyl acetate/hexanes as eluant) afforded the title compound. LC/MS: 358.1 (M+1-BOC)

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07388019B2
Source dataset	uspto-grants-2008_06
ORD ID	ord-81457b8ecf6543988f4194de0641e27a
Source note	uspto-grants-2008_06