Triethylamine → tert-butyl 4-{(1R)-1-[(1-benzofuran-2-ylcarbonyl)amino]ethyl}benzoate

To a 2-dram vial was added triethylamine (0.10 mL, 0.72 mmol), HATU (0.068 g, 0.18 mmol), benzofuran-2-carboxylic acid (0.029 g, 0.18 mmol), and DCM (2 mL). The solution was stirred at rt for 30 min then transferred to another 2-dram vial containing solid tert-butyl-4-[(1R)-1-aminoethyl]benzoate hydrochloride. The mixture was stirred at rt for 16 h. To the reaction was then added DCM (3 mL) and water (1 mL). After separation, the aqueous layer was extracted with DCM (2×3 mL). The combined organic phases were concentrated to dryness to give crude tert-butyl 4-{(1R)-1-[(1-benzofuran-2-ylcarbonyl)amino]ethyl}benzoate as a brown solid. LC-MS: (FA) ES+ 366.

1. stirringThe mixture was stirred at rt for 16 h
2. customAfter separation
3. extractionthe aqueous layer was extracted with DCM (2×3 mL)
4. concentrationThe combined organic phases were concentrated to dryness

ORD record

ord-d539d717a90b4767ba79252e74e8dc86

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382197B2