反应 #1001500

反应方程式

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester

5-bromopyridin-2-ol

triphenylphosphine

diisopropyl diazodicarboxylate

→

title compound

收率 57.3%

2-[(4-{2-[(5-bromopyridin-2-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester

收率 57.3%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   温度cooling
2. 2
   浓缩The reaction mixture was concentrated under reduced pressure, and hexane (about 10 mL)
3. 3
   workup.ADDITIONwas added
4. 4
   其他The precipitated crystals were removed by filtration
5. 5
   其他the solvent of the filtrate was evaporated under reduced pressure
6. 6
   其他The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1)

实验过程

2-{[4-(2-Hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (2.12 g) synthesized in Example 4 and 5-bromopyridin-2-ol (1.22 g) were dissolved in tetrahydrofuran (20 mL), triphenylphosphine (2.02 g) and diisopropyl diazodicarboxylate (40% toluene solution, 4.14 ml) were added under ice-cooling, and the mixture was stirred at room temperature for 12 hr. The reaction mixture was concentrated under reduced pressure, and hexane (about 10 mL) was added. The precipitated crystals were removed by filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=5:1) to give the title compound (1.84 g) as a pale-yellow oil.

来源