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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
ノート
印刷プレビュー

反応式

HRID 1925527 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 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

生成物 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
収率 34%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-21d24335de2147848014e93a08cda325
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08178679B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート