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

HRID 856195ノート

反応式

HRID 856195 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:25][C:26]1[CH:41]=[CH:40][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][N:34]([C:37](Cl)=[O:38])[CH2:33][CH2:32]2)=[CH:28][CH:27]=1>CN(C)C1C=CN=CC=1.C1(C)C=CC=CC=1.C(OCC)(=O)C>[Cl:25][C:26]1[CH:41]=[CH:40][C:29]([CH2:30][N:31]2[CH2:32][CH2:33][N:34]([C:37]([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:38])[CH2:35][CH2:36]2)=[CH:28][CH:27]=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 230815584-(4-Chlorobenzyl)piperazine-1-carbonylchloride

生成物 1

HCID 69480796(R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl 4-(4-chlorobenzyl)piperazine-1-carboxylate収率 48%

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-methyl)propyl-4-nitroimidazole prepared in Example 10 (2.28 g, 9.66 mmol), N,N-diisopropylethylamine (2.81 ml, 16.10 mmol) and 4-dimethylaminopyridine (0.20 g, 1.61 mmol) were added to a suspension of 4-(4-chlorobenzyl)piperazine-1-carbonylchloride (2.20 g, 8.05 mmol) in toluene (30 ml) followed by stirring 100° C. for 3 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-chlorobenzyl)piperazine-1-carboxylate (1.82 g, yield 48%) as a 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-c9ba43734fa54765a6182071b9ef7c76
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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