Diisopropylethylamine → Ethyl (2S)-3-(4-{2-[butyl(2,3-dimethoxybenzyl)amino]-2-oxoethoxy}phenyl)-2-ethoxypropanoate

To a solution of N-butyl-N-(2,3-dimethoxybenzyl)amine (1.23 g, 5.5 mmol) and {4-[(2S)-2,3-diethoxy-3-oxopropyl]phenoxy}acetic acid (1.48 g, 5.0 mmol) in methylene chloride (50 mL) at 0° C. were added N,N-diisopropylethylamine (2.0 mL, 11.5 mmol) followed by O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.93 g, 6.0 mmol) and the reaction mixture was stirred overnight and then concentrated in vacuo. The residue was taken up in ethyl acetate (200 mL) and the organic phase was washed with saturated aqueous NaHCO3 (3×100 mL), 5% HCl (3×100 mL), and brine (100 mL), dried over Na2SO4, and concentrated in vacuo. Purification on silica gel (120 g) with methanol (0-2% gradient) in methylene chloride as the eluent and collection of pure fractions afforded 1.07 g (43%) of a pale yellow oil.

1. concentrationconcentrated in vacuo
2. washthe organic phase was washed with saturated aqueous NaHCO3 (3×100 mL), 5% HCl (3×100 mL), and brine (100 mL)
3. dry with materialdried over Na2SO4
4. concentrationconcentrated in vacuo
5. customPurification on silica gel (120 g) with methanol (0-2% gradient) in methylene chloride
6. customas the eluent and collection of pure fractions

ORD record

ord-7d776acb036e49aa9658b1bfdc3461f6

Source dataset

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07488844B2