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Sodium Carbonate → tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate

HRID 2203492
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HRID 2203492 반응식
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[C:12]([O:16][C:17](=[O:42])[NH:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[CH:30][C:29]2[N:28]=[CH:27][C:26]3[N:32]=[C:33]([CH2:38][O:39][CH2:40][CH3:41])[N:34]([CH2:35][CH2:36][CH3:37])[C:25]=3[C:24]=2[CH:23]=1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl>[CH2:40]([O:39][CH2:38][C:33]1[N:34]([CH2:35][CH2:36][CH3:37])[C:25]2[C:24]3[CH:23]=[C:22]([O:21][CH2:20][CH2:19][NH:18][C:17](=[O:42])[O:16][C:12]([CH3:13])([CH3:14])[CH3:15])[CH:31]=[CH:30][C:29]=3[N+:28]([O-:9])=[CH:27][C:26]=2[N:32]=1)[CH3:41]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 131731977tert-butyl[2-(2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate

생성물 1

HCID 68973926tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate수율 64.9%

시약·촉매·용매 1

HCID 6212
Chloroform
용매
2회

실험 절차

mCPBA (60% pure, 12.76 g, 44.36 mmol) was added in one portion to a solution of tert-butyl[2-(2-ethoxymethyl-1-propyl-1H-imidazo[4,5-c]quinolin-8-yloxy)ethyl]carbamate (14.4 g, 33.6 mmol) and chloroform (150 mL); the reaction mixture was stirred for 30 minutes. The reaction mixture was then poured into saturated aqueous sodium carbonate (100 mL) and stirred for 30 minutes. Chloroform (250 mL) was added, and the organic fraction was washed sequentially with 5% aqueous sodium carbonate, water, and brine; dried over magnesium sulfate; filtered; and concentrated under reduced pressure. The resulting red oil was triturated with ethyl acetate to provide 9.7 g of tert-butyl 2-[(2-ethoxymethyl-5-oxido-1-propyl-1H-imidazo[4,5-c]quinolin-8-yl)oxy]ethylcarbamate as a peach-colored powder.

후처리

  1. stirringstirred for 30 minutes
  2. washthe organic fraction was washed sequentially with 5% aqueous sodium carbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationand concentrated under reduced pressure
  6. customThe resulting red oil was triturated with ethyl acetate

출처 및 근거

ORD 기록
ord-b2f6e5290f9b44c2a0e98929e8b2f5de
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09365567B2

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