تفاعل #59869
ord-c127fee4ad9e44e5947c45fbf65f39b4
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1workup.ADDITIONwas added dropwise at −55° C. to −50° C. for 10 minutes in a nitrogen atmosphere
- 2أخرىThe reaction was terminated
- 3workup.ADDITIONby adding 12 ml of a saturated aqueous solution of sodium hydrogen carbonate at the same temperature
- 4استخلاصThe mixture was extracted with 50 ml of chloroform twice
- 5تجفيفthe organic layer was dried over anhydrous sodium sulfate
- 6تركيزconcentrated
- 7أخرىThe obtained crude product
- 8أخرىwas purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol=1/0-4/1 gradient)
- 9تركيزdesired fractions were concentrated
- 10أخرىThe obtained white foam was re-precipitated with chloroform and diethyl ether
- 11ترشيحfiltered
الإجراء التجريبي
To a toluene (8.1 ml) and methanol (0.9 ml) solution of the 2-(((3-methyl-4-((8-methyl-1,4,7,9-tetraoxaspiro[4.5]dec-8-yl)methoxy)pyridin-2-yl)methyl)thio)-1H-benzimidazole (372 mg, 0.84 mmol) obtained in the step (5f), a toluene (2.7 ml) and methanol (0.3 ml) solution of 3-chloroperbenzoic acid (200 mg, 0.76 mmol as the content was regarded as 65%) was added dropwise at −55° C. to −50° C. for 10 minutes in a nitrogen atmosphere. The mixture was stirred at −60° C. to −50° C. for 1.5 hours. The reaction was terminated by adding 12 ml of a saturated aqueous solution of sodium hydrogen carbonate at the same temperature. The mixture was extracted with 50 ml of chloroform twice, and then, the organic layer was dried over anhydrous sodium sulfate and concentrated. The obtained crude product was purified by silica gel column chromatography (NH silica gel, elution solvent: ethyl acetate/methanol=1/0-4/1 gradient) and desired fractions were concentrated. The obtained white foam was re-precipitated with chloroform and diethyl ether and filtered. The operation was repeated twice to obtain the title compound (148 mg, 38.4% yield) as a white solid.