反応 #74883

反応方程式

water

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

phenacyl bromide

tributyl phosphine

→

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

収率 80.7%

溶媒

N,N-dimethylformamide

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate (3×100 ml.)
2. 2
   洗浄The combined organic phases were washed with water (2×100 mls.)
3. 3
   その他evaporated to a yellow oil which
4. 4
   その他was chromatographed on silica gel eluting with 33% ethyl acetate in benzene

実験手順

(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.

出典