Triethylamine → HCID 131722214, compound

Participants

Reaction Steps

1.03 g (5.28 mmole) of 3-isopropoxyphenylacetic acid were dissolved in 50 ml of methylene chloride, and 1.10 g (5.76 mmole) of WSC.HCl (Water Soluble Carbodiimide.HCl), 780 mg (5.76 mmole) of 1-hydroxybenzotriazol.H2O, 1.61 ml (11.5 mmole) of triethylamine, and 1.50 g (4.80 mmole) of (2R)-(3,4-dichlorophenyl)-2-(2-hydroxyethyl)morpholine hydrochloride [prepared as described in Example 76(c)] were added to the resulting solution, in that order. The mixture was then stirred at room temperature for 15 hours under a nitrogen atmosphere. At the end of this time, a saturated aqueous solution of ammonium chloride was added to the reaction mixture, which was then extracted with ethyl acetate. The organic extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the resulting residue was purified by silica gel column chromatography, using a gradient elution method, with mixtures of hexane and ethyl acetate ranging from 3:1 to 2:1 by volume as the eluent, to give 1.81 g of the title compound.

Provenance & Evidence