تفاعل #9588

معادلة التفاعل

p-Toluenesulfonyl chloride

3-Chloroperoxybenzoic acid

tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate

Ammonium hydroxide

→

tert-butyl[4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo [4,5-c]quinolin-1-ylmethyl)benzyl]carbamate

المذيبات

chloroform

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةcooled with an ice bath
2. 2
   workup.STIRRINGthe reaction was stirred for 10 minutes
3. 3
   أخرىThe cooling bath was removed
4. 4
   workup.STIRRINGthe mixture was stirred for an additional 16 hours
5. 5
   أخرىThe layers were separated
6. 6
   استخلاصthe aqueous fraction was extracted with dichloromethane
7. 7
   غسيلThe combined organic fractions were washed sequentially with water and saturated aqueous sodium chloride
8. 8
   تجفيفdried over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated under reduced pressure
11. 11
    أخرىPurification of the residue
12. 12
    أخرىby flash column chromatography (CMA/chloroform) and subsequent recrystallization from acetonitrile

الإجراء التجريبي

3-Chloroperoxybenzoic acid (2.91 g, 9.3 mmol, 55% pure) was added to a solution of tert-butyl[4-(7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-ylmethyl)benzyl]carbamate (3.2 g, 6.1 mmol) in chloroform (60 mL). The reaction was stirred for 1 hour and then cooled with an ice bath. Ammonium hydroxide (40 mL) was added and the reaction was stirred for 10 minutes. p-Toluenesulfonyl chloride (1.16 g, 6.1 mmol) was added in two portions. The cooling bath was removed and the mixture was stirred for an additional 16 hours. The layers were separated and the aqueous fraction was extracted with dichloromethane. The combined organic fractions were washed sequentially with water and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification of the residue by flash column chromatography (CMA/chloroform) and subsequent recrystallization from acetonitrile yielded 1.15 g of tert-butyl[4-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo [4,5-c]quinolin-1-ylmethyl)benzyl]carbamate as a tan solid.

المصدر