Triethylamine → tert-butyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)phenyl)carbamate

https://huagongshe.com/reaction/2202047

Participants

Role	Name	HCID	Charge
Reactant	Triethylamine	HCID 8471	—
Reactant	1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide	HCID 15908	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	3-(((Tert-butoxy)carbonyl)amino)benzoic acid	HCID 854162	—
Reactant	1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol	HCID 16790720	—
Solvent	Dichloromethane	HCID 6344	—
Product	tert-butyl(3-((3-(3,4-dihydroisoquinolin-2(1H)-yl)-2-hydroxypropyl)carbamoyl)phenyl)carbamate	HCID 90245499	71.6%

Reaction Conditions

Temperature	25 °C

Reaction Steps

To a solution of 3-((tert-butoxycarbonyl)amino)benzoic acid (2.5 g, 10.5 mmol) in DCM (25 mL) was added EDCI (3.0 g, 15.7 mmol), HOBt (2.1 g, 15.7 mmol), Et3N (2.1 g, 21 mmol) and 1-amino-3-(3,4-dihydroisoquinolin-2(1H)-yl)propan-2-ol (2.2 g, 10.5 mmol). The mixture was stirred at 25° C. for 16 h. The reaction solution was washed with water and extracted with DCM. The organic layer was concentrated, and the residue was purified by column chromatography to give the title product (3.2 g, 71%). LCMS (m/z): 426.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09365519B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-44c9a898f0e349e186a7ac9c50b1c43b
Source note	uspto-grants-2016_06