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Sodium Iodide → 5-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

HRID 1925502
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HRID 1925502 반응식
[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH2:22])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[CH2:23]([O:30][C:31]1[CH:32]=[CH:33][C:34]([C@@H:42]([O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH2:43]Br)=[C:35]2[C:40]=1[NH:39][C:38](=[O:41])[CH:37]=[CH:36]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])O.[Na+].[I-].[Na+]>CS(C)=O.O>[C:1]12([CH2:11][CH2:12][O:13][C:14]3[CH:15]=[C:16]([CH2:20][CH2:21][NH:22][CH2:43][C@@H:42]([C:34]4[CH:33]=[CH:32][C:31]([O:30][CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[C:40]5[C:35]=4[CH:36]=[CH:37][C:38](=[O:41])[NH:39]5)[O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[CH:17]=[CH:18][CH:19]=3)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 516892Sodium BicarbonateHCID 15606253(R)-8-(benzyloxy)-5-(2-bromo-1-((tert-butyldimethylsilyl)oxy)ethyl)quinolin-2(1H)-oneHCID 67520349(2-{3-[2-(1-Adamantyl)ethoxy]phenyl}ethyl)amine

생성물 1

HCID 675208935-((1R)-2-[(2-{3-[2-(1-adamantyl)ethoxy]phenyl}ethyl)amino]-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-8-(benzyloxy)quinolin-2(1H)-one

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

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온도
120 °C

실험 절차

To a solution of Intermediate 31 (0.51 g, 1.7 mmol) in dimethyl sulfoxide (1.5 mL) and (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (1.06 g, 2.17 mmol) in dimethyl sulfoxide (2 mL) was added sodium hydrogen carbonate (0.53 g, 6.37 mmol) and sodium iodide (0.970 g, 6.47 mmol). The reaction mixture was stirred at 120° C. for 2 hours. The reaction was poured into water and filtered. The crude was purified by column chromatography with silica gel, eluting by methylen chloride giving the title compound as a solid (0.84 g, 63%). MS (M+): 708.

후처리

  1. filtrationfiltered
  2. customThe crude was purified by column chromatography with silica gel
  3. washeluting by methylen chloride giving the title compound as a solid (0.84 g, 63%)

출처 및 근거

ORD 기록
ord-6931393a02d04f579a6fd8859e8dce34
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178679B2

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