Ethyl Acetate → tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate

Participants

Role	Name	HCID	Charge
Reactant	Ethyl Acetate	HCID 8857	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	tert-butyl ((2S)-1-((5-((4-(benzyloxy)benzoyl)amino)-4-chloropyridin-2-yl)oxy)propan-2-yl)carbamate	HCID 86731322	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-butyl ((2S)-1-((2-(4-(benzyloxy)phenyl) [1,3]oxazolo[4,5-c]pyridin-6-yl)oxy)propan-2-yl)carbamate	HCID 86731321	35.7%

Reaction Conditions

Temperature	160 °C

Reaction Steps

A suspension of tert-butyl ((2S)-1-((5-((4-(benzyloxy)benzoyl)amino)-4-chloropyridin-2-yl)oxy)propan-2-yl)carbamate (2.50 g), potassium carbonate (1.35 g) and copper(I) iodide (93.9 mg) in DMF (20 mL) was stirred at 160° C. for 3.5 hr. The reaction mixture was subjected to silica gel chromatography (NH, ethyl acetate), washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained solid was washed with ethyl acetate/hexane to give the title compound (830 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09133129B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-ce181cad8c294b9ba999ee9c450d9795
Source note	uspto-grants-2015_09