Triethylamine → HCID 69527450, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of (2R,3S)-2-amino-1,3-butanediol 4-methylbenzenesulfonate (2.3 g) in nitromethane (32 mL) was added triethylamine (1.1 mL) and triethyl orthoformate (1.3 mL). The mixture was stirred at 110° C. for 0.5 hour and cooled in an ice-bath. A mixture of ethyl α-amino-α-cyanoacetate 4-methylbenzenesulfonate (2.0 g), triethylamine (1.0 mL) and acetonitrile (32 mL) was added to the reaction mixture, and the whole was stirred at 100° C. for 8 hours. The mixture was concentrated in vacuo and the residue was purified by column chromatography on silica gel (gradient elution; 10:1 to 5:1 chloroform-methanol containing 1% ammonium hydroxide) to give the crude product, which was further purified by column chromatography on silica gel (gradient elution; 20:1 to 10:1 to 5:1 ethyl acetate-1% ammonium hydroxide/methanol) to give ethyl 5-amino-1-[(1R,2S)-2-hydroxy-1-(hydroxymethyl)propyl]-1H-imidazole-4-carboxylate (1.0 g).

Provenance & Evidence