Water → [(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl] 4-(1,3-dioxolan-2-ylmethyl)benzoate

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride	HCID 2723939	—
Reactant	4-(1,3-Dioxolan-2-ylmethyl)benzoic acid	HCID 24726991	—
Reactant	(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide	HCID 71092494	—
Catalyst	4-(Dimethylamino)pyridine	HCID 14284	—
Solvent	Dichloromethane	HCID 6344	—
Product	[(1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethyl] 4-(1,3-dioxolan-2-ylmethyl)benzoate	HCID 86720696	97%

Reaction Steps

To a solution of 4-((1,3-dioxolan-2-yl)methyl)benzoic acid (362 mg, 1.05 mmol) in DCM (9 mL) was added (1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol (200 mg, 0.96 mmol) followed by DMAP (58 mg, 0.48 mmol) and EDC.HCl (396 mg, 1.9 mmol). The mixture was allowed to stir a room temperature for 18 hours and then water (20 mL) and DCM (20 mL) were added and the organic phase was passed through a hydrophobic frit. The solvent was removed in vacuo and the crude material was purified by silica gel column chromatography, eluting with 30-100% EtOAc in DCM, to afford the title compound as an off-white solid (497 mg, 97%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09090606B2
Source dataset	uspto-grants-2015_07
ORD ID	ord-27f85e65983d4f3fb14a301f613016ca
Source note	uspto-grants-2015_07