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Dimethylformamide → [4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester

HRID 1064611
ノート
印刷プレビュー

反応式

HRID 1064611 の反応式
[N:1]1([CH2:9][C:10]([OH:12])=[O:11])[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].C(N1C=CN=C1)(N1[CH:19]=[CH:18]N=C1)=O.[CH2:25]([OH:35])[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1.CN([CH:39]=[O:40])C>>[CH2:18]([O:11][C:10](=[O:12])[CH2:9][N:1]1[CH:8]=[CH:7][C:5]([NH:6][C:39]([O:35][CH2:25][C:26]2[CH:34]=[CH:33][C:32]3[O:31][CH2:30][O:29][C:28]=3[CH:27]=2)=[O:40])=[N:4][C:2]1=[O:3])[CH3:19]
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

5

反応物 4

HCID 6228DimethylformamideHCID 10322Piperonyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 21868458(4-Amino-2-oxo-2H-pyrimidin-1-yl)-acetic acid

生成物 1

HCID 68524231[4-N-(Piperonyloxycarbonyl)-cytosin-1-yl]-acetic acid ethyl ester収率 96%

反応条件

温度
100 °C

実験手順

The reaction mixture of (cytosin-1-yl)-acetic acid (3.94 g, 20 mmol) and 1,1′-carbonyldiimidazole (4.86 g, 30 mmol) in DMF was stirred for 25 min. at 100° C. Then, piperonyl alcohol (6.08 g, 40 mmol) was added to the reaction mixture. The resulting reaction mixture was allowed to cool to room temperature for 2 h. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate (100 mL). The solution was washed with water (100 mL×2), dried over MgSO4, and filtered. The filtrate was concentrated in vacuo and treated with ethyl ether to afford white solid. The solid was filtered off and dried in vacuo to give the desired product (7.20 g, 96%). 1H-NMR (500 MHz; DMSO-d6) δ 10.77 (s, 1H), 8.04 (d, 1H), 7.04 (d, 1H), 7.00 (s, 1H), 6.92 (s, 2H), 6.02 (s, 2H), 5.09 (s, 2H), 4.61 (s, 2H), 4.15 (q, 2H), 1.19 (t, 3H).

後処理

  1. customThe resulting reaction mixture
  2. temperatureto cool to room temperature for 2 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (100 mL)
  5. washThe solution was washed with water (100 mL×2)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. additiontreated with ethyl ether
  10. customto afford white solid
  11. filtrationThe solid was filtered off
  12. customdried in vacuo

出典と根拠

ORDレコード
ord-958182d48e514af89223823579fb856b
出典データセット
uspto-grants-2005_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06969766B2

反応ノート

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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