Реакция #1435690

Уравнение реакции

2-chloro-3-(benzyloxy)-propionic acid chloride

glycine benzyl ester-p-toluenesulfonic acid salt

triethylamine

hydrochloric acid

→

1-Benzyloxy-5-(benzyloxycarbonyl)-2-chloro-3-oxo-4-azapentane

Растворители

water

methylene chloride

Условия реакции

Обработка

1. 1
   ДругоеThe organic phase is separated
2. 2
   Промывкаwashed once each with 300 ml of 5% aqueous hydrochloric acid, 300 ml of 5% aqueous soda solution and 400 ml of water
3. 3
   ДругоеThe organic phase is dried on magnesium sulfate
4. 4
   Другоеevaporated to dryness in a vacuum
5. 5
   ДругоеThe residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone=15/5/1)

Методика

76 g (326.1 mmol) of 2-chloro-3-(benzyloxy)-propionic acid chloride (produced according to Inorg. Chem. Vol. 31; 2422, 1992) is added in drops to 100 g (296.4 mmol) of glycine benzyl ester-p-toluenesulfonic acid salt and 33.0 g (326.1 mmol) of triethylamine in 400 ml of methylene chloride at 0° C., and it is stirred for 2 hours at this temperature. 500 ml of ice water is added, and the water phase is set at pH 2 with 10% aqueous hydrochloric acid. The organic phase is separated, washed once each with 300 ml of 5% aqueous hydrochloric acid, 300 ml of 5% aqueous soda solution and 400 ml of water. The organic phase is dried on magnesium sulfate and evaporated to dryness in a vacuum. The residue is chromatographed on silica gel (mobile solvent: methylene chloride/hexane/acetone=15/5/1).

Источник