تفاعل #1001700

معادلة التفاعل

diisopropyl azodicarboxylate

diisopropyl azodicarboxylate

triphenylphosphine

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

triphenylphosphine

4-(4-nitrophenyl)phenol

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title compound

المردود 74.1%

2-methyl-2-[(4-{2-[(4′-nitrobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester

المردود 74.1%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooling for 5 min
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature overnight
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 3.5 hr
4. 4
   تركيزThe reaction mixture was concentrated
5. 5
   استخلاصextracted with ethyl acetate
6. 6
   غسيلThe organic layer was washed with aqueous sodium hydroxide solution and saturated brine
7. 7
   تجفيفdried over anhydrous magnesium sulfate
8. 8
   أخرىThe solvent was evaporated under reduced pressure
9. 9
   أخرىthe obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

الإجراء التجريبي

To a solution of 2-{[4-(2-hydroxyethyl)-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (2.7 g) synthesized in Example 4 in tetrahydrofuran (15 ml) were added triphenylphosphine (2.5 g) and 4-(4-nitrophenyl)phenol (12.1 g), and the mixture was stirred under ice-cooling for 5 min. To the solution was added diisopropyl azodicarboxylate (40% toluene solution, 4.7 ml), and the mixture was stirred at room temperature overnight. To the solution were further added triphenylphosphine (1.2 g) and diisopropyl azodicarboxylate (40% toluene solution, 2.4 ml), and the mixture was stirred at room temperature for 3.5 hr. The reaction mixture was concentrated, extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (3.3 g) as a pale-brown solid.

المصدر