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

Sodium hydride → 2-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole

HRID 2243849
ノート
印刷プレビュー

反応式

HRID 2243849 の反応式
CC1(CN2C=C([N+]([O-])=O)N=C2)CO1.C(OC(N1CCNCC1)=O)(C)(C)C.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([CH2:40][C:41]([OH:53])([CH3:52])[CH2:42][N:43]2[CH:47]=[C:46]([N+:48]([O-:50])=[O:49])[N:45]=[C:44]2Br)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[H-].[Na+]>CC(O)C.CN(C=O)C.O>[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][N:37]([CH2:40][C:41]2([CH3:52])[O:53][C:44]3=[N:45][C:46]([N+:48]([O-:50])=[O:49])=[CH:47][N:43]3[CH2:42]2)[CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28]
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

8

反応物 4

HCID 24758Sodium hydrideHCID 143452tert-Butyl piperazine-1-carboxylateHCID 686533884-[3-(2-Bromo-4-nitro-imidazol-1-yl)-2-hydroxy-2-methyl-propyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 866206311-(2-methyl-oxiranylmethyl)-4-nitro-1H-imidazole

生成物 1

HCID 230810802-(4-Tert-butoxycarbonylpiperazin-1-yl)methyl-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazole
収率 50.1%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3776Isopropanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A solution of 1-(2-methyl-oxiranylmethyl)-4-nitro-1H-imidazole (1.5 g, 5.72 mmol) and piperazine-1-carboxylic acid tert-butyl ester (1.1 g, 5.72 mmol) is dissolved in IPA and heated to 60° C. for 24 h. The solution is concentrated and partitioned between water and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated. The resulting solution of 4-[3-(2-bromo-4-nitro-imidazol-1-yl)-2-hydroxy-2-methyl-propyl]-piperazine-1-carboxylic acid tert-butyl ester (1.1 g, 2.46 mmol) in DMF (15 ml) was treated with sodium hydride (148 mg, 3.69 mmol) and stirred for 3 h at 60° C. The mixture was diluted with water and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated. The residue is purified by silica gel chromatography to give 4-(2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazol-2-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester (453 mg, 50%) of as a light yellow oil. ESI MS m/z 367 (M+Na+); 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 4.30 (d, J=10 Hz, 1H), 3.92 (d, J=10 Hz, 1H), 3.45-3.02 (m, 4H), 2.86 (d, J=14.8 Hz, 1H), 2.70-2.39 (m, 4H), 2.55 (d, J=14.8, 1H), 1.58 (s, 3H), 1.45 (s, 9H).

後処理

  1. concentrationThe solution is concentrated
  2. custompartitioned between water and ethyl acetate
  3. dry with materialThe organic layer is dried over sodium sulfate
  4. concentrationconcentrated
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel chromatography

出典と根拠

ORDレコード
ord-f62c75ffb03e47df9d72b2a1ec70b4e9
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678791B2

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