Methanol → HCID 53998134, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 100.0 g of methyl (2S)-2-ethanamido-3-(4-methanamidophenyl)propanoate in 3000 cm3 of tetrahydrofuran at 20° C. with stirring are added, under nitrogen, 378 cm3 of a 2 M solution of borane/methyl sulphide in tetrahydrofuran such that the temperature of the reaction mixture is maintained below 25° C. At the end of the addition, the reaction mixture is kept stirring for 1 hour at 25° C. and 1000 cm3 of methanol are then added dropwise. At the end of the addition of the methanol, the mixture is stirred at 25° C. under nitrogen for 16 hours and then concentrated under reduced pressure (20 kPa) at a temperature of 40° C. At the end of the concentration, the mixture is allowed to return to 25° C. under nitrogen and 1000 cm3 of dichloromethane and 1000 cm3 of saturated aqueous sodium chloride solution are then added. The mixture is stirred for 30 minutes at 25° C. and is then separated by settling of the phases. The lower organic phase is removed and dried over anhydrous sodium sulphate. After filtration of the sodium sulphate, the solution is concentrated at 30° C. under reduced pressure (20 kPa).

Provenance & Evidence