4-Chlorobenzenesulfonyl chloride → cis-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide

HRID 7027

反応式

HRID 7027 の反応式
[NH2:1][C@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[C:8]([NH2:10])=[O:9].C(N(CC)CC)C.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>ClCCl>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:1][C@H:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]2[C:8]([NH2:10])=[O:9])(=[O:27])=[O:26])=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 2724813cis-2-Aminocyclohexanecarboxamide

生成物 1

HCID 69655699cis-2-(4-Chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide収率 45.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of cis-2-aminocyclohexanecarboxylic acid amide (2.0 g, 14.0 mmol), and triethylamine (3.9 mL, 28 mmol) in dichloromethane (100 mL) was added 4-chlorobenzenesulfonyl chloride (2.95 g, 14.0 mmol). The resulting solution was stirred at room temperature for 18 h. The reaction was then diluted with dichloromethane (200 mL) and washed with H2O, 1.0 M HCl, brine, and dried over Na2SO4. Further purification by flash chromatography (silica gel, 1% to 10% MeOH/CHCl3) afforded cis-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (2.0 g) as a white solid in 45% yield over three steps: 1H NMR (DMSO-d6) δ 7.82 (m, 2 H), 7.63 (m, 2 H), 7.56 (d, 1 H, J=7.0 Hz), 7.22 (s br, 1 H), 6.80 (s br, 1 H), 3.43 (m, 1 H), 2.37 (m,1 H), 1.72 (m, 2 H), 1.45 (m, 3 H), 1.15 (m, 3 H); MS m/e 317.05 (M+H)+.

後処理

  1. washwashed with H2O, 1.0 M HCl, brine
  2. dry with materialdried over Na2SO4
  3. customFurther purification by flash chromatography (silica gel, 1% to 10% MeOH/CHCl3)

出典と根拠

ORDレコード
ord-5401af972bfd4b98b671d0bcf01afd38
出典データセット
uspto-grants-2006_08
特許番号
US07084178B2

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