反応 #56014

反応方程式

benzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

1,5-diazabicyclo[5.4.0]undec-5-ene

→

benzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

収率 94.7%

溶媒

ethylacetate

反応条件

後処理

1. 1
   洗浄After a period of 15 minutes the reaction mixture was washed with brine
2. 2
   乾燥dried over sodium sulphate
3. 3
   濃縮It was concentrated

実験手順

A suspension of benzyl 3-chloro-3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]heptane-2-carboxylate (54) (0.020 g) in ethylacetate (2 ml) was stirred at room temperature under argon and treated with 1,5-diazabicyclo[5.4.0]undec-5-ene (0.009 g). After a period of 15 minutes the reaction mixture was washed with brine and dried over sodium sulphate. It was concentrated to give a single diastereoisomer of benzyl 3-ethylsulphinyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (55) (0.017 g) as a gum; νmax (CHCl3) 2980, 1795 and 1730 cm-1 ; τ(d6 -acetone) 2.5-2.8 (5H, m, phenyl), 4.78 (2H, s, benzyl CH2), 5.71 (1H,tdd J9,5 and 3 Hz, C5-H), 6.49 (1H, dd J17 and 5 Hz, C6-H), 6.82 (2H, d J 9 Hz, C4-H2), 6.84 (1H, dd J17 and 3 Hz, C6-H), 7.13 and 7.15 (2H, 2q J71/2 Hz, SCH2) and 8.80 (3H, t J71/2 Hz, CH3).

出典