Diisopropylethylamine → methyl (S)-alpha-[(S)-alpha-[(t-butylsulphonyl)methyl]hydrocinnamamido]imidazolepropionate

Participants

Reaction Steps

15.8 g (65.5 mmol) of L-histidine methyl ester dihydrochloride, 18.6 g of (S)-α-[(t-butylsulphonyl)-methyl]hydrocinnamic acid, 28.9 g of BOP and 35.8 ml of Hunig base are dissolved in 400 ml of acetonitrile and subsequently stirred at room temperature for 12 hours. After the usual working-up the crude produce is purified by flash chromatography on silica gel, whereby there are obtained 28 g (98%) of methyl (S)-α-[(S)-α-[(t-butylsulphonyl)methyl]hydrocinnamamido]imidazolepropionate as a resin, Rf value 0.25 in a 20:1 mixture of methylene chloride and methanol, MS: 435 (M)+.

Provenance & Evidence