1,2-Dichloroethane → HCID 58286517、化合物

HRID 2098457ノート

反応式

HRID 2098457 の反応式
[C@H:1]12[CH2:7][C@H:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24](O)=[O:25].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>C(Cl)Cl.O>[NH:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([N:5]1[CH2:6][C@@H:1]2[CH2:7][C@H:4]1[CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:25]

参加物

8

反応物 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 2332402-Benzimidazolecarboxylic acidHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

生成物 1

HCID 58286517HCID 58286517、化合物収率 63.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 1,1-dimethylethyl (1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (18.3 g, 92.5 mmol), 1H-benzimidazole-2-carboxylic acid, (15.0 g, 92.5 mmol), EDC (21.3 g, 111 mmol), HOBt (2.5 g, 18.5 mmol), NMM (28 g, 277.5 mmol) in CH2Cl2 (250 mL) was stirred at room temperature for 18 h. The reaction was diluted with water and CH2Cl2 then washed with sat. NaHCO3 (200 mL) and brine (200 mL). The solution was dried over anhydrous Na2SO4 and concentrated to give a crude product which was purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1) to give the title compound (20 g) as a white solid. LCMS (m/z): 343.2 (M+H).

後処理

  1. washthen washed with sat. NaHCO3 (200 mL) and brine (200 mL)
  2. dry with materialThe solution was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto give a crude product which
  5. customwas purified by column chromatography on silica gel (petroleum ether/ethyl acetate: 2/1)

出典と根拠

ORDレコード
ord-ae0677e762b04f509b11776a5f3bcacf
出典データセット
uspto-grants-2013_05
特許番号
US08450484B2

反応ノート

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