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Sodium Iodide → 8-(benzyloxy)-5-(1-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one

HRID 1925527
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HRID 1925527 반응식
[CH3:1][C:2]([NH2:24])([CH3:23])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][C:13]23[CH2:22][CH:17]4[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]4)[CH2:14]2)[CH2:20]3)[CH:5]=1.[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([C@@H:44]([O:47][Si:48]([C:51]([CH3:54])([CH3:53])[CH3:52])([CH3:50])[CH3:49])[CH2:45]Br)=[C:37]2[C:42]=1[NH:41][C:40](=[O:43])[CH:39]=[CH:38]2)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[I-].[Na+].C(=O)([O-])O.[Na+]>CN1CCCC1=O.O>[CH2:25]([O:32][C:33]1[CH:34]=[CH:35][C:36]([CH:44]([O:47][Si:48]([C:51]([CH3:52])([CH3:54])[CH3:53])([CH3:50])[CH3:49])[CH2:45][NH:24][C:2]([CH3:1])([CH3:23])[CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[C:6]([O:10][CH2:11][CH2:12][C:13]34[CH2:22][CH:17]5[CH2:16][CH:15]([CH2:21][CH:19]([CH2:18]5)[CH2:20]3)[CH2:14]4)[CH:5]=2)=[C:37]2[C:42]=1[NH:41][C:40](=[O:43])[CH:39]=[CH:38]2)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1
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 675204661,1-Dimethyl-2-(3-(1-adamantyl)ethoxyphenyl)ethylamine

생성물 1

HCID 675205018-(benzyloxy)-5-(1-(tert-butyldimethylsilyloxy)-2-(2-methyl-1-(3-(2-(1-adamantyl)ethoxy)phenyl)propan-2-ylamino)ethyl)quinolin-2(1H)-one
수율 34%

시약·촉매·용매 2

HCID 962Water용매HCID 13387N-methyl-2-pyrrolidone용매

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온도
120 °C

실험 절차

To a solution of Intermediate 87 (0.981 g, 3.0 mmol) and (R)-8-(benzyloxy)-5-(2-bromo-1-(tert-butyldimethylsilyloxy)ethyl)quinolin-2(1H)-one (1.463 g, 2.99 mmol) in N-methylpyrrolidinone (5 mL) was added sodium iodide (0.471 g, 3.14 mmol) and sodium hydrogencarbonate (0.352 g, 4.19 mmol). The reaction mixture was heated at 120° C. for 4 hours and poured into excess water. The organic layer was extracted with diethyl ether and washed with water. The solvent was removed under reduced pressure and the crude was purified by column chromatography with silica gel, eluting with dichloromethane/methanol (from 90:1 to 90:2) to give 0.748 g (34% yield) of the title compound.

후처리

  1. extractionThe organic layer was extracted with diethyl ether
  2. washwashed with water
  3. customThe solvent was removed under reduced pressure
  4. customthe crude was purified by column chromatography with silica gel
  5. washeluting with dichloromethane/methanol (from 90:1 to 90:2)

출처 및 근거

ORD 기록
ord-21d24335de2147848014e93a08cda325
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08178679B2

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