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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1042934Generated: October 25, 2026

Ethyl Acetate → phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester

https://huagongshe.com/reaction/1042934

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
ReactantPotassium di-tert-butyl phosphateHCID 23674467—
Reactant2,6-dichloro-N-[4-(1-chloromethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamideHCID 86675421—
CatalystTetrabutylammonium IodideHCID 67553—
SolventDimethylformamideHCID 6228—
Productphosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl esterHCID 71149943—

Reaction Conditions

Temperature70 °C

Reaction Steps

2,6-Dichloro-N-[4-(1-chloromethyl-2-oxo-1,2-dihydro-pyridin-4-yl)-benzyl]-benzamide from the previous step was dissolved in 50 mL DMF. Potassium carbonate (1 g) was added followed by potassium di(t-butyl)phosphate (2 g) and tetrabutylammonium iodide (50 mg). The mixture was stirred at 70° C. for four hours after which it was poured into 300 mL ethyl acetate. The organic phase was washed with water and brine, dried with magnesium sulfate and evaporated under vacuum. The crude product was further purified by silica gel chromatography (eluent: ethyl acetate), giving phosphoric acid di-tert-butyl ester 4-{4-[(2,6-dichloro-benzoylamino)-methyl]-phenyl}-2-oxo-2H-pyridin-1-ylmethyl ester as a colorless oil which slowly crystallized.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08558001B2
Source datasetuspto-grants-2013_10
ORD IDord-e44cac3e8c1145db86fe9fb197a5c8e6
Source noteuspto-grants-2013_10