Reaktion #1001500

Reaktionsgleichung

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

Ausbeute 57.3%

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

Ausbeute 57.3%

Lösungsmittel

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle