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Diisopropylcarbodiimide → HCID 68309694、化合物

HRID 1048848
ノート
印刷プレビュー

反応式

HRID 1048848 の反応式
[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C.[C:37]1([C@H:47]([NH2:49])[CH3:48])[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1>ClCCl>[CH2:1]([N:8]1[C:13](=[O:14])[CH2:12][O:11][CH2:10][CH:9]1[C:15]([NH:49][C@@H:47]([C:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][CH:38]=1)[CH3:48])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 135433704-Benzyl-5-oxomorpholine-3-carboxylic acid

生成物 1

HCID 68309694HCID 68309694、化合物収率 60.7%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

To a stirred solution of 4-benzyl-5-oxomorpholine-3-carboxylic acid (Organic and Bio-Organic Chemistry (1972-1999); (1985); 2577-2580) (500 mg, 2.12 mmole) in dichloromethane (15 mL), HOBt (430 mg, 3.19 mmole) and DIPC (287 μL, 3.19 mmole) were added at room temperature. The reaction mixture was stirred for 15 min, then (R)-1-(naphthalen-1-yl)ethanamine (400 μL, 2.57 mmole) was added to the reaction mixture and stirred overnight. Solid separated out was filtered, washed with dichloromethane (2×15 mL), filtrate collected and washed with brine solution (2×15 mL) and DM water. The organic layer was concentrated to get crude amide and which was further purified by flash chromatography (n-Hexane:ethyl acetate, 8:3) to get title compound (500 mg). m/z 389.2

後処理

  1. stirringstirred overnight
  2. customSolid separated out
  3. filtrationwas filtered
  4. washwashed with dichloromethane (2×15 mL), filtrate
  5. customcollected
  6. washwashed with brine solution (2×15 mL) and DM water
  7. concentrationThe organic layer was concentrated
  8. customto get crude amide and which
  9. customwas further purified by flash chromatography (n-Hexane:ethyl acetate, 8:3)

出典と根拠

ORDレコード
ord-529186db08f249099d389417d75b0c35
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09382216B2

反応ノート

読み込み中…

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