4-Toluenesulfonyl chloride → HCID 86626167, 화합물

HRID 2383157노트

반응식

HRID 2383157 반응식
C1C=C(Cl)C=C(C(OO)=O)C=1.[C:12]([O:16][C:17](=[O:46])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:35]2[C:34]3[CH:33]=[CH:32][C:31]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)=[CH:30][C:29]=3[N:28]=[CH:27][C:26]=2[N:25]=[C:24]1[CH2:44][CH3:45])([CH3:15])([CH3:14])[CH3:13].[OH-].[NH4+:48].C1(C)C=CC(S(Cl)(=O)=O)=CC=1>C(Cl)(Cl)Cl>[C:12]([O:16][C:17](=[O:46])[NH:18][CH2:19][CH2:20][CH2:21][CH2:22][N:23]1[C:35]2[C:34]3[CH:33]=[CH:32][C:31]([O:36][CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)=[CH:30][C:29]=3[N:28]=[C:27]([NH2:48])[C:26]=2[N:25]=[C:24]1[CH2:44][CH3:45])([CH3:15])([CH3:14])[CH3:13]

참가 물질

6

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 14923Ammonium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 86626166HCID 86626166, 화합물

생성물 1

HCID 86626167HCID 86626167, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

mCPBA (10.6 g, 33.7 mmol) was added in one portion to a solution of tert-butyl[4-(7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate (16.0 g, 33.7 mmol) in chloroform (270 mL). After the reaction was stirred for 1.5 hours, ammonium hydroxide (270 mL) was added. The mixture was stirred for 15 minutes, and p-toluenesulfonyl chloride (6.42 g, 33.7 mmol) was added in three portions. The reaction was stirred for 18 hours. The layers were separated, and the aqueous layer was extracted with dichloromethane. The combined organic fractions were washed with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from acetonitrile to afford 9.73 g of tert-butyl[4-(4-amino-7-benzyloxy-2-ethyl-1H-imidazo[4,5-c]quinolin-1-yl)butyl]carbamate as a gray powder.

후처리

  1. stirringThe mixture was stirred for 15 minutes
  2. stirringThe reaction was stirred for 18 hours
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined organic fractions were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-c0e3486ba407473caeece47b452ace24
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263594B2

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