Chloroacetyl chloride → HCID 54373183, compound

3.60 g (9.88 mmole) of 1-amino-4-t-butyldimethylsilyloxy-(2R)-(3,4-dichlorophenyl)-2-butanol [prepared as described in Example 1(e)], 1.64 ml (11.8 mmole) of triethylamine and 121 mg (0.99 mmole) of 4-dimethylaminopyridine were dissolved in 100 ml of methylene chloride, and 0.94 ml (11.8 mmole) of chloroacetyl chloride were added dropwise, whilst ice-cooling. The mixture was then stirred at the same temperature for 2 hours. At the end of this time, 100 ml of methylene chloride were added to the reaction mixture, and the resulting mixture was washed with ice-cooled 10% w/v aqueous hydrochloric acid, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order. It was then dried over anhydrous magnesium sulfate. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by silica gel flash column chromatography, using a gradient elution method, with mixtures of ethyl acetate and hexane ranging from 1:5 to 1:2 by volume as the eluent, to obtain 3.32 g (yield 76%) of the title compound as a colorless oil.

1. temperaturecooling
2. washthe resulting mixture was washed with ice-
3. temperaturecooled 10%
4. dry with materialIt was then dried over anhydrous magnesium sulfate
5. customThe solvent was then removed by distillation under reduced pressure
6. customthe resulting residue was purified by silica gel flash column chromatography
7. washa gradient elution method

ORD record

ord-601dbf55b4fc4544b90b83b6507824e5

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448247B1