Triethylamine → HCID 10642198, compound

Participants

Reaction Steps

To a solution of methyl ((2S)-2-[N-(benzyloxycarbonyl)amino]-5-hydroxy-pentanoate (1.84 g, 6.98 mmol) in dichloromethane (27 ml) cooled to -10° C. under argon was added triethylamine (1.057 g, 10.47 mmol) and then methanesulphonyl chloride (0.99 g, 8.72 mmol) over a 2 minute period. Stirring was continued for 35 minutes while the temperature was maintained below 0° C. The reaction mixture was then diluted with dichloromethane (200 ml) and washed with water (100 ml), 10% aqueous citric acid (2×100 ml), saturated aqueous sodium bicarbonate (100 ml) and dilute brine (100 ml), dried (Na2SO4) and concentrated in vacuo to a yellow oil residue. Purification by column chromatography, on elution with 1:1 v/v ethyl acetate/hexanes, afforded methyl (2S)-2-{N-(benzyloxycarbonyl)amino!-5-(methylsulphonyloxy)-pentanoate as a colourless viscous oil (2.40 g, 96%);

Provenance & Evidence