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Triethylamine → 4-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 1894367
ノート
印刷プレビュー

反応式

HRID 1894367 の反応式
[CH:1]([NH:14][S:15]([CH2:18][CH2:19][CH2:20]Cl)(=[O:17])=[O:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(N(CC)CC)C>CN(C)C=O>[C:25]([O:24][C:22]([N:29]1[CH2:34][CH2:33][N:32]([CH2:20][CH2:19][CH2:18][S:15](=[O:17])(=[O:16])[NH:14][CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:31][CH2:30]1)=[O:23])([CH3:28])([CH3:26])[CH3:27]
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

5

反応物 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 436538363-Chloro-propane-1-sulfonic acid benzhydryl-amide

生成物 1

HCID 672053494-[3-(Benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester収率 52.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

In a three-neck round bottom flask equipped with argon inlet was charged with anhydrous dimethylformamide and 3-chloro-propane-1-sulfonic acid benzhydryl-amide (893 mg, 2.76 mmol). 1-Boc-piperazine (771 mg, 4.14 mmol, Aldrich) was added, followed by triethylamine (0.77 mL, 5.52 mmol). The mixture was stirred at 60° C. overnight. It was then heated at 120° C. for 10 min and at 180° C. for 15 min using the microwave synthesizer. Upon cooling, the reaction mixture was concentrated, and the residue was diluted with ethyl acetate. The organic layer was washed with water, brine, and concentrated. Purification of the crude residue by flash column chromatography gave 4-[3-(benzhydryl-sulfamoyl)-propyl]-piperazine-1-carboxylic acid tert-butyl ester as yellow oil (688 mg).

後処理

  1. customIn a three-neck round bottom flask equipped with argon inlet
  2. temperatureIt was then heated at 120° C. for 10 min and at 180° C. for 15 min
  3. temperatureUpon cooling
  4. concentrationthe reaction mixture was concentrated
  5. additionthe residue was diluted with ethyl acetate
  6. washThe organic layer was washed with water, brine
  7. concentrationconcentrated
  8. customPurification of the crude residue by flash column chromatography

出典と根拠

ORDレコード
ord-737c2672e4fc4d93b43fc158d42b3cd8
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08513239B2

反応ノート

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