反应详情

(S)-N6-Benzyloxycarbonyllysine (1.5 kg) was slurried in methylene chloride (7.5 l) and chlorotrimethylsilane (1.36 l) added over 10 minutes. The mixture was heated under reflux for 30 minutes to give a solution which was cooled to 3° C. before simultaneously adding diisopropylethylamine (1.87 l) and methanesulphonyl chloride (435 ml) at such a rate as to keep the temperature below 25° C. The reaction was stirred for a further 2.5 hours then poured into 2 M aqueous hydrochloric acid solution. The layers were separated and the methylene chloride phase was washed with 2 M aqueous hydrochloric acid solution followed by water. The solvent was removed under reduced pressure and replaced with n-butyl acetate. The solution was cooled and the resulting crystalline material was collected by filtration, washed with n-butyl acetate and dried under reduced pressure to provide the title compound (1.63 kg), m.p. 83.5-84° C. [α]D25−13.4° (c=1, methanol). Found: C,50.23; H,6.40; N,7.76.

1. temperatureThe mixture was heated
2. temperatureunder reflux for 30 minutes
3. customto give a solution which
4. customthe temperature below 25° C
5. customThe layers were separated
6. washthe methylene chloride phase was washed with 2 M aqueous hydrochloric acid solution
7. customThe solvent was removed under reduced pressure
8. temperatureThe solution was cooled
9. filtrationthe resulting crystalline material was collected by filtration
10. washwashed with n-butyl acetate
11. customdried under reduced pressure