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tert-Butyldimethylsilyl chloride → N-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine

HRID 1035489
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HRID 1035489 반응식
[CH3:1][CH:2]([CH3:20])[C@H:3]([NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH2:4][OH:5].[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Si:21]([O:5][CH2:4][C@@H:3]([NH:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=[CH:9][C:8]=1[N+:17]([O-:19])=[O:18])[CH:2]([CH3:20])[CH3:1])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]
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참가 물질

5

반응물 2

HCID 28928tert-Butyldimethylsilyl chlorideHCID 67156854(2S)-3-methyl-2-[(3-nitroquinolin-4-yl)amino]butan-1-ol

생성물 1

HCID 67157210N-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine수율 97.3%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine
용매

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온도
56 °C

실험 절차

(2S)-3-Methyl-2-[(3-nitroquinolin-4-yl)amino]butan-1-ol (3.97 g, 14.4 mmol) was dissolved in 15 mL of dry pyridine and treated with tert-butyldimethylsilyl chloride (2.40 g, 15.9 mmol) and a catalytic amount of 4-(dimethylamino)pyridine (DMAP) (176 mg, 1.44 mmol). The reaction mixture was stirred under N2 and heated to 56° C. After 2 days, the reaction mixture was concentrated under reduced pressure. The resulting solid was partitioned between 100 mL of H2O and 100 mL of ethyl acetate. The layers were separated and the organic portion was washed with H2O and brine. The organic portion was then dried over Na2SO4, filtered and concentrated under reduced pressure. Chromatography (SiO2, 20% ethyl acetate/hexanes) gave N-[(1S)-1-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2-methylpropyl]-3-nitroquinolin-4-amine (5.46 g) as a yellow syrup.

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe resulting solid was partitioned between 100 mL of H2O and 100 mL of ethyl acetate
  3. customThe layers were separated
  4. washthe organic portion was washed with H2O and brine
  5. dry with materialThe organic portion was then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-4ecdfbb6cb904bbf8a59b3c5c1b1b524
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546383B2

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