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Diethyl Ether → 1,1-Dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate

HRID 2109071
ノート
印刷プレビュー

反応式

HRID 2109071 の反応式
[H-].[Na+].[CH:3]1([CH2:6][NH:7][C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:9]=2)[CH2:5][CH2:4]1.Br[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(OCC)C>CN(C=O)C>[C:12]([C:11]1[CH:14]=[CH:15][C:8]([N:7]([CH2:6][CH:3]2[CH2:5][CH2:4]2)[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:9][C:10]=1[C:16]([F:17])([F:18])[F:19])#[N:13]
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

6

反応物 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 114818514-[(Cyclopropylmethyl) amino]-2-(trifluoromethyl)benzonitrile

生成物 1

HCID 113142081,1-Dimethylethyl N-[4-cyano-3-(trifluoromethyl)phenyl]-N-(cyclopropylmethyl)glycinate収率 74%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
7.5 °C

実験手順

Sodium hydride (60%, 2.0 g, 50 mmol) was added to a stirred solution of 4-[(cyclopropylmethyl)amino]-2-(trifluoromethyl)benzonitrile (6.0 g, 25 mmol), and tert-butyl bromoacetate (6.82 g, 35 mmol) in 20 mL of DMF at 0° C. over 20 minutes. The mixture was then stirred at 5-10° C. for 30 minutes. Diethyl ether (200 mL) was added to the mixture and the resulting slurry was extracted with water (3×50 mL). The organic phase was dried (MgSO4), filtered, and then concentrated under reduced pressure. The residue was purified with silica gel chromatography (eluent:hexane-EtOAc; 3:1) to obtain 6.55 g (74%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.59 (d, J=8.8 Hz, 1H), 6.92 (d, J=2.6 Hz, 1H), 6.77 (dd, J=8.8, 2.7 Hz, 1H), 4.10 (s, 2H), 3.33 (d, J=6.6 Hz, 2H), 1.43 (s, 9H), 1.05 (m, 1H), 0.62 (m, 2H), 0.26 (m, 2H).

後処理

  1. extractionthe resulting slurry was extracted with water (3×50 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified with silica gel chromatography (eluent:hexane-EtOAc; 3:1)

出典と根拠

ORDレコード
ord-09a1bfd32b52453fa3d565982acfe567
出典データセット
uspto-grants-2009_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07514470B2

反応ノート

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