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

HRID 856199ノート

反応式

HRID 856199 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.[F:25][C:26]([F:44])([F:43])[C:27]1[CH:32]=[CH:31][C:30]([NH:33][CH:34]2[CH2:39][CH2:38][N:37]([C:40](Cl)=[O:41])[CH2:36][CH2:35]2)=[CH:29][CH:28]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:43][C:26]([F:25])([F:44])[C:27]1[CH:28]=[CH:29][C:30]([NH:33][CH:34]2[CH2:39][CH2:38][N:37]([C:40]([O:13][CH2:12][C@@:11]([OH:15])([CH3:14])[CH2:10][N:3]3[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]3[Cl:1])=[O:41])[CH2:36][CH2:35]2)=[CH:31][CH:32]=1

参加物

7

反応物 3

HCID 81531DiisopropylethylamineHCID 16099121(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-methylpropane-1,2-diolHCID 230810884-(4-Trifluoromethylphenylamino)piperidine-1-carbonylchloride

生成物 1

HCID 69479082(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate収率 61%

試薬・触媒・溶媒 3

HCID 142844-(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 (1.54 g, 7.01 mmol), N,N-diisopropylethylamine (1.63 ml, 9.34 mmol) and 4-dimethylaminopyridine (0.11 g, 0.93 mmol) were added to a suspension of 4-(4-trifluoromethylphenylamino)piperidine-1-carbonylchloride (1.43 g, 4.67 mmol) in toluene (30 ml) followed by stirring at 100° C. for 2.5 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 (methylene chloride/ethyl acetate=9/1) to afford (R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-trifluoromethylphenylamino)piperidine-1-carboxylate (1.44 g, yield 61%) as a light yellow 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 (methylene chloride/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-49a77821bf574a3bab0f823a01f7a3b3
出典データセット
uspto-grants-2007_08
特許番号
US07262212B2

反応ノート

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