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Diisopropylethylamine → (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-tert-butoxycarbonylpiperazine-1-carboxylate

HRID 856194
ノート
印刷プレビュー

反応式

HRID 856194 の反応式
[Cl:1][C:2]1[N:3]([CH2:10][C@:11]([OH:15])([CH3:14])[CH2:12][OH:13])[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.C(N(CC)C(C)C)(C)C.Cl[C:26]([N:28]1[CH2:33][CH2:32][N:31]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:30][CH2:29]1)=[O:27]>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:37]([O:36][C:34]([N:31]1[CH2:30][CH2:29][N:28]([C:26]([O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]2[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]2[Cl:1])=[O:27])[CH2:33][CH2:32]1)=[O:35])([CH3:40])([CH3:38])[CH3:39]
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

7

反応物 3

HCID 81531DiisopropylethylamineHCID 11334154Tert-butyl 4-(chlorocarbonyl)piperazine-1-carboxylateHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diol

生成物 1

HCID 69480637(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-tert-butoxycarbonylpiperazine-1-carboxylate収率 69%

試薬・触媒・溶媒 3

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 1140Toluene溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

(R)-2-Chloro-1-(2,3-dihydroxy-2-methylpropyl)-4-nitroimidazole prepared in Example 10 (4.43 g, 18.79 mmol), N,N-diisopropylethylamine (4.68 ml, 26.84 mmol) and 4-dimethylaminopyridine (0.33 g, 2.68 mmol) were added to a suspension of tert-butyl 4-chlorocarbonylpiperazine-1-carboxylate (3.34 g, 13.42 mmol) in toluene (70 ml), and the resulting mixture was stirred at 100° C. for 4.5 hours. The reaction mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/methylene chloride/ethyl acetate=45/45/10) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-tert-butoxycarbonylpiperazine-1-carboxylate (4.12 g, yield 69%) as a colorless oil.

後処理

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (n-hexane/methylene chloride/ethyl acetate=45/45/10)

出典と根拠

ORDレコード
ord-56c4624867a34681b4efbec8a416bcc8
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

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