(2S)-2-amino-5-(((tert-butoxy)carbonyl)amino)pentanoic acid → N2-[(4-{(2S)-3-(Allyloxy)-2-[(tert-butoxycarbonyl)amino]-3-oxopropyl}phenoxy)carbonyl]-N5-(tert-butoxycarbonyl)ornithine

関与物質

反応条件

反応手順

3.00 g (6.16 mmol) of the compound from example 1A was dissolved in 60 ml dichloromethane. 1.43 g (6.16 mmol) N5-(tert-Butoxycarbonyl)-L-ornithine was added. The reaction mixture was split into 3 portions. The portions were heated for 30 min in a sealed tube at 75° C. in a microwave synthesizer. The combined reaction mixture was extracted with approx. 500 ml saturated ammonium chloride solution. The aqueous phase was twice back extracted with approx. 30 ml dichloromethane each. The combined organic phases were extracted with approx. 50 ml brine and dried over sodium sulfate. The solvent was removed under reduced pressure. The raw product was dissolved in dichloromethane and chromatographed over approx. 500 ml silica gel. Solvents used were dichloromethane, dichloromethane/methanol 20/1 to dichloromethane/methanol 1/1. The product-containing fractions were combined and concentrated to dryness under reduced pressure. This gave 2.29 g (3.50 mmol, 57% of theory, 89% purity) of the desired product.

情報源と証拠