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Sodium hydride → (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-tertbutoxycarbonylpiperazine-1-carboxylate

HRID 856202
ノート
印刷プレビュー

反応式

HRID 856202 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C@@:18]([OH:30])([CH3:29])[CH2:19][N:20]2[CH:24]=[C:23]([N+:25]([O-:27])=[O:26])[N:22]=[C:21]2Cl)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][CH2:17][C@:18]2([CH3:29])[O:30][C:21]3=[N:22][C:23]([N+:25]([O-:27])=[O:26])=[CH:24][N:20]3[CH2:19]2)=[O:15])[CH2:10][CH2:9]1)=[O:7])([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

4

反応物 2

HCID 24758Sodium hydrideHCID 69480637(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-tert-butoxycarbonylpiperazine-1-carboxylate

生成物 1

HCID 69481521(R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-tertbutoxycarbonylpiperazine-1-carboxylate収率 59.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To the solution of (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-tertbutoxycarbonylpiperazine-1-carboxylate prepared in Example 87 (4.12 g, 9.20 mmol) in DMF (30 ml), sodium hydride (0.44 g, 11.04 mmol) was added followed by stirring for 1 hour with cooling on ice-bath. Ice-water was added to the reaction mixture, and the precipitates were filtered off, purified by silica gel column chromatography (ethyl acetate) and then washed with isopropanol to afford (R)-2-methyl-6-nitro-2,3-dihydroimidazo[2,1-b]oxazol-2-ylmethyl 4-tertbutoxycarbonylpiperazine-1-carboxylate (2.24 g, yield 59%) as a white solid.

後処理

  1. temperaturewith cooling on ice-bath
  2. filtrationthe precipitates were filtered off
  3. custompurified by silica gel column chromatography (ethyl acetate)
  4. washwashed with isopropanol

出典と根拠

ORDレコード
ord-33a7d78ae0414ab890232c04b509f3ae
出典データセット
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07262212B2

反応ノート

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