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Acetic Acid → {2-[3'-(2-Cyano-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester

HRID 643508
ノート
印刷プレビュー

反応式

HRID 643508 の反応式
[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25](Cl)[N:24]=3)[CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[C-]#N.[K+].[N:34]12CCN(CC1)C[CH2:35]2.CC(O)=O>O.CS(C)=O>[C:1]([O:5][C:6](=[O:30])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]3[CH:28]=[CH:27][N:26]=[C:25]([C:35]#[N:34])[N:24]=3)[CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]
参加物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 176Acetic AcidHCID 9032Potassium CyanideHCID 9237DabcoHCID 86622896{2-[3'-(2-Chloro-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester

生成物 1

HCID 68579160{2-[3'-(2-Cyano-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 679
Dimethyl Sulfoxide
溶媒
HCID 962Water溶媒

実験手順

A mixture of {2-[3′-(2-chloro-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester (150 mg), potassium cyanide (76 mg) and 1,4-diazabicyclo[2,2,2]octane (13 mg) in water (0.4 ml) and DMSO (2 ml) is left at 5° C. for 4 h. This mixture is acidified with AcOH to pH 4-5, quenched with brine and extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate, the solvent is evaporated and the crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1 to afford pure {2-[3′-(2-cyano-pyrimidin-4-yloxy)-biphenyl-4-yl]-ethyl}carbamic acid tert-butyl ester.

後処理

  1. customquenched with brine
  2. extractionextracted twice with diethyl ether
  3. dry with materialThe combined organic phases are dried over sodium sulfate
  4. customthe solvent is evaporated
  5. customthe crude product is purified on silica (15 g) with cyclohexane/EtOAc=5/1

出典と根拠

ORDレコード
ord-6d0517714e3541ef931cb018e1326217
出典データセット
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07700605B2

反応ノート

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