Potassium Hydroxide → 2-[(6-Tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester

A solution of KOH (0.266 g, 4.11 mmol) in ethanol (14 mL) was added to a solution of 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid diethyl ester (1.82 g, 4.11 mmol) in ethanol (12 mL) and methylene chloride (13 mL) at 0° C. The mixture was stirred overnight at room temperature. More KOH (80 mg dissolved in 3 mL ethanol) was added at 0° C. The reaction mixture was stirred for additional 18 h. The mixture was concentrated under reduced pressure and ethyl acetate, and 0.5 M HCl were added to the residue. The organic layer was washed with brine and dried. After filtration and evaporation in vacuo, the residue was suspended in hexane. Filtration of the crystals gave 2-[(6-tert-butoxycarbonylamino-pyridin-3-yl)-phenyl-methyl]-malonic acid monoethyl ester (1.7 g, 98%).

1. stirringThe reaction mixture was stirred for additional 18 h
2. concentrationThe mixture was concentrated under reduced pressure and ethyl acetate, and 0.5 M HCl
3. additionwere added to the residue
4. washThe organic layer was washed with brine
5. customdried
6. filtrationAfter filtration and evaporation in vacuo
7. filtrationFiltration of the crystals

ORD record

ord-96bd72ab02c549c9994fa9edd37dec7e

Source dataset

uspto-grants-2006_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07071175B1