ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Water → Ethyl 2-(1-(4-(Benzyloxy)-2-nitrophenyl)-2-oxopyrrolidin-3-yl)acetate

HRID 1964091
ノート
印刷プレビュー

反応式

HRID 1964091 の反応式
[O:1]=[C:2]1[CH:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:5][CH2:4][NH:3]1.[H-].[Na+].[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26](F)=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CN(C=O)C>[CH2:15]([O:22][C:23]1[CH:28]=[CH:27][C:26]([N:3]2[CH2:4][CH2:5][CH:6]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:2]2=[O:1])=[C:25]([N+:30]([O-:32])=[O:31])[CH:24]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=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

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 442030064-(Benzyloxy)-1-fluoro-2-nitrobenzeneHCID 66847687Ethyl 2-(2-oxopyrrolidin-3-yl)acetate

生成物 1

HCID 67249168Ethyl 2-(1-(4-(Benzyloxy)-2-nitrophenyl)-2-oxopyrrolidin-3-yl)acetate収率 26.5%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
0 °C

実験手順

Ethyl 2-(2-oxopyrrolidin-3-yl)acetate (1.77 g, 10.34 mmol) was dissolved in DMF (20 mL) and cooled to 0° C. Sodium hydride (60% in mineral oil, 0.414 g, 10.34 mmol) was added. After stirring for several min, the reaction was allowed to warm to room temperature and stirred for 10 min. 4-(Benzyloxy)-1-fluoro-2-nitrobenzene (2.56 g, 10.34 mmol) was added and the mixture was stirred at room temperature for 21 h. The reaction was poured into water and acidified to pH 5 with 1.0 M HCL. The aqueous mixture was extracted three times with EtOAc and the combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography to provide the title compound (1.09 g). LCMS m/z=399.4 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.27 (t, J=7.2 Hz, 3H), 1.97-2.01 (m, 1H), 2.46-2.59 (m, 2H), 2.95 (dd, J=12.9, 3.8 Hz, 1H), 2.96-3.06 (m, 1H), 3.69-3.76 (m, 1H), 3.79-3.88 (m, 1H), 4.17 (q, J=7.1 Hz, 2H), 5.13 (s, 2H), 6.90 (d, J=2.5 Hz, 1H), 6.94 (dd, J=9.0, 2.7 Hz, 1H), 7.37-7.42 (m, 5H), 8.04 (d, J=9.1 Hz, 1H).

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 10 min
  3. stirringthe mixture was stirred at room temperature for 21 h
  4. extractionThe aqueous mixture was extracted three times with EtOAc
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-2106ea46a933461caf1ffd6ee3a3fc76
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08415484B2

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