反応 #50255

反応方程式

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane

Triethylamine

Thiolacetic acid

triethylamine

2-fluoro-1-methylpyridinium toluene-4-sulfonate

→

10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane

溶媒

benzene

acetone

反応条件

後処理

1. 1
   温度the reaction is heated
2. 2
   温度to reflux for 2 hours
3. 3
   その他The solvent is then removed
4. 4
   その他the crude product is partitioned between methylene chloride and water
5. 5
   抽出the aqueous phase is extracted several times with methylene chloride
6. 6
   乾燥The combined organic layers are dried (MgSO4)
7. 7
   その他the solvent is evaporated
8. 8
   その他The crude product is purified by silica gel chromatography (15% ethyl acetate/hexane)

実験手順

3-t-Butoxycarbonylmethyl-10-hydroxymethyl-2-oxo-1-azacyclodecane (0.50 g, 1.67 mmol) is dissolved in acetone (5.0 mL) and benzene (5.0 mL). Triethylamine (0.26 mL, 1.9 mmol) is added, followed by 2-fluoro-1-methylpyridinium toluene-4-sulfonate (0.54 g, 1.9 mmol), and the reaction is stirred at room temperature for 90 minutes. Thiolacetic acid (0.14 mL, 1.9 mmol) and more triethylamine (0.26 mL, 1.9 mmol) are added, and the reaction is heated to reflux for 2 hours. The solvent is then removed, the crude product is partitioned between methylene chloride and water, and the aqueous phase is extracted several times with methylene chloride. The combined organic layers are dried (MgSO4) and the solvent is evaporated. The crude product is purified by silica gel chromatography (15% ethyl acetate/hexane) to give 10-(acetylthiomethyl)-3-t-butoxycarbonylmethyl-2-oxo-1-azacyclodecane, MS: M+1=358.

出典