تفاعل #2016103

معادلة التفاعل

ethyl 4-(2-(((4-(((8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-1,2,3,4-tetrahydro-1-benzazocine-5-yl)carbonyl)amino)phenyl)sulfanyl)methyl)-imidazol-1-yl)butanoate

3-chloroperbenzoic acid

→

ethyl 4-(2-(((4-(((8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-1,2,3,4-tetrahydro-1-benzoazocine-5-yl)carbonyl)amino)phenyl)sulfinyl)methyl)imidazol-1-yl)butanoate

المردود 77.6%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThen, dry ice-acetone bath was removed
2. 2
   workup.ADDITIONan aqueous sodium thiosulfate solution was added with vigorous stirring
3. 3
   workup.STIRRINGAfter stirring the mixture at room temperature for 30 minutes
4. 4
   workup.ADDITIONwater was added
5. 5
   استخلاصthe mixture was extracted with ethyl acetate
6. 6
   غسيلThe organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine
7. 7
   تجفيفwas dried with magnesium sulfate
8. 8
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
9. 9
   أخرىthe resulting residue was separated
10. 10
    أخرىpurified with basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate)
11. 11
    أخرىrecrystallized from hexane-ethyl acetate

الإجراء التجريبي

To a solution of ethyl 4-(2-(((4-(((8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-1,2,3,4-tetrahydro-1-benzazocine-5-yl)carbonyl)amino)phenyl)sulfanyl)methyl)-imidazol-1-yl)butanoate (400 mg) in dichloromethane (10 ml) was added dropwise a 70% solution of 3-chloroperbenzoic acid (144 mg) in dichloromethane (10 ml) at −78° C. As such, the mixture was stirred for 1 hour. Then, dry ice-acetone bath was removed and an aqueous sodium thiosulfate solution was added with vigorous stirring. After stirring the mixture at room temperature for 30 minutes, water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated sodium bicarbonate solution and saturated brine, and was dried with magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was separated and purified with basic silica gel column chromatography (hexane:ethyl acetate=1:1→ethyl acetate), and recrystallized from hexane-ethyl acetate to give ethyl 4-(2-(((4-(((8-(4-(2-butoxyethoxy)phenyl)-1-isobutyl-1,2,3,4-tetrahydro-1-benzoazocine-5-yl)carbonyl)amino)phenyl)sulfinyl)methyl)imidazol-1-yl)butanoate (317 mg) as yellow crystals (Compound 54).

المصدر