Sodium Hydroxide → 3-[4-[(1,1-Dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester

Tetrabutyl ammonium sulfate (3.0 g, 9 mmol) was added to a biphasic mixture consisting of 10% aqueous sodium hydroxide (75 mL), 2-[(diphenylmethylene)amino]acetic acid benzyl ester (3.05 g, 9.3 mmol) and 1,1-dimethylethyl 4-bromomethylbenzoate (3.0 g, 9 mmol) in dichloromethane (58 mL). After several hours of vigorous stirring at room temperature, the reaction mixture was diluted with ether (300 mL) and the layers were separated. The organic layer was washed with water (3×30 mL), dried (K2CO3) and filtered. Concentration provided an oil that was purified by HPLC on silica gel (the columns were pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes) eluting with a mixture of hexanes-ethyl acetate to give rac.-2-](diphenylmethylene)amino]-3-[4-[(1,1-dimethylethoxy)carbonyl]phenyl]propanoic acid benzyl ester, (1.7 g, 3 mmol) in 36% yield.

1. customthe layers were separated
2. washThe organic layer was washed with water (3×30 mL)
3. dry with materialdried (K2CO3)
4. filtrationfiltered
5. concentrationConcentration
6. customprovided an oil that
7. customwas purified by HPLC on silica gel (the columns
8. additionwere pre-treated with 10% triethylamine/hexanes, ethyl acetate and finally hexanes)
9. washeluting with a mixture of hexanes-ethyl acetate

ORD record

ord-64e2a740e9364e50820298a4b8d45b2d

Source dataset

uspto-grants-1993_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05182263