Dimethylformamide → HCID 54464324, compound

Participants

Reaction Conditions

Reaction Steps

J (S)-2-(3-Nitrophenyl)-N-[(R)-2-hydroxy-1-phenylethyl]propionamide may be prepared in the following manner: 17.2 cm3 of oxalyl chloride are added slowly to a mixture containing 39.0 g of (RS)-2-(3-nitrophenyl)propionic acid and 0.5 cm3 of N,N-dimethylformamide in 400 cm3 of 1,2-dichloroethane. The reaction medium is stirred for 3 hours at a temperature in the region of 20° C. and then concentrated under reduced pressure. The residue is dissolved in 150 cm3 of 1,2-dichloroethane and added to a solution of 27.4 g of (R)-2-phenylglycinol while the temperature of the reaction medium is maintained below 10° C. The reaction mixture is stirred for 12 hours at a temperature in the region of 20° C., and is then washed successively with 1000 cm3 of distilled water, 500 cm3 of normal aqueous hydrochloric acid solution, twice 500 cm3 of distilled water and 500 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate and concentrated under reduced pressure. The two diastereoisomers obtained are separated by chromatography on silica [eluent: methylene chloride/ethyl acetate (70:30 by volume)]. The fractions containing each of the two diastereoisomers are pooled and concentrated under reduced pressure. 21.0 g of (R)-2-(3-nitrophenyl)-N-[(R)-2-hydroxy-1-phenylethyl]propionamide (first elution product), melting point 135° C., and 19.0 g of (S)-2-(3-nitrophenyl)-N-[(R) -2-hydroxy-1-phenylethyl]propionamide (second elution product), melting point 150° C., are thereby obtained.

Provenance & Evidence