Реакция #74883

Уравнение реакции

water

(3R,4R)-4(2'-Methyl-n-propyldithio)-3-phenylacetamidoazetidin-2-one

phenacyl bromide

tributyl phosphine

→

(3R,4R)-3-phenylacetamido-4-phenacylthioazetidin-2-one

Выход 80.7%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Экстракцияextracted with ethyl acetate (3×100 ml.)
2. 2
   ПромывкаThe combined organic phases were washed with water (2×100 mls.)
3. 3
   Другоеevaporated to a yellow oil which
4. 4
   Другоеwas chromatographed on silica gel eluting with 33% ethyl acetate in benzene

Методика

(3R,4R)-4(2'-Methyl-n-propyldithio)-3-phenylacetamidoazetidin-2-one (0.5 g., 0.0015 mole), phenacyl bromide (1.0 g., 0.005 mole), and tributyl phosphine (0.8 ml., 0.0032 mole) were stirred in N,N-dimethylformamide (10 ml.) for 0.25 hours. The reaction mixture was poured into water (100 ml.) and extracted with ethyl acetate (3×100 ml.). The combined organic phases were washed with water (2×100 mls.) and evaporated to a yellow oil which was chromatographed on silica gel eluting with 33% ethyl acetate in benzene to yield (3R,4R)-3-phenylacetamido-4-phenacylthioazetidin-2-one (0.429 g., 78%). The constants were as described previously for compound B in Example 3.

Источник