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Benzyloxycarbonylglycine → HCID 131736174、化合物

HRID 1052505
ノート
印刷プレビュー

反応式

HRID 1052505 の反応式
CCN(C(C)C)C(C)C.[NH2:10][N:11]1[CH:15]=[CH:14][C:13]([Br:16])=[C:12]1[C:17]([NH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18].[CH2:26]([O:33][C:34]([NH:36][CH2:37][C:38](O)=[O:39])=[O:35])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(P1(=O)OP(CCC)(=O)OP(CCC)(=O)O1)CC>C(OCC)(=O)C>[Br:16][C:13]1[CH:14]=[CH:15][N:11]([NH:10][C:38](=[O:39])[CH2:37][NH:36][C:34](=[O:35])[O:33][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:12]=1[C:17](=[O:18])[NH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
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

6

反応物 4

HCID 14349Benzyloxycarbonylglycine2 回HCID 81531Diisopropylethylamine2 回HCID 111923Propylphosphonic anhydride2 回HCID 70979311HCID 70979311、化合物

生成物 1

HCID 131736174HCID 131736174、化合物収率 92.1%

試薬・触媒・溶媒 1

HCID 8857
Ethyl Acetate
溶媒
4 回

反応条件

温度
0 °C

実験手順

DIEA (10.5 ml, 60 mmol) was added at 0° C. over a mixture of 1-amino-3-bromo-N-phenyl-1H-pyrrole-2-carboxamide (5.1 g, 18 mmol) and 2-(benzyloxycabonylamino)acetic acid (5.33 g, 25 mmol) in anhydrous ethyl acetate (100 ml). After 15 min T3P® solution (50% AcOEt, 15 ml) was slowly added and stirred 20 min at 0° C. and then at room temperature overnight. Further DIEA (5 ml, 30 mmol), 2-(benzyloxycabonylamino)acetic acid (2.66 g, 25 mmol) and T3P® solution (50% AcOEt, 7 ml) were added and the reaction mixture was stirred at room temperature overnight. More ethyl acetate was added and the reaction crude was washed with water and brine, dried over magnesium sulphate and the solvent was removed under vacuum. The residue was purified by flash chromatography using Isolera® Purification System (0-40%, hexane-AcOEt) to give 7.81 g (41% yield) of the final product with a purity of 45% that was used in the next step without further purification.

後処理

  1. customat room temperature
  2. customovernight
  3. stirringthe reaction mixture was stirred at room temperature overnight
  4. customthe reaction crude
  5. washwas washed with water and brine
  6. dry with materialdried over magnesium sulphate
  7. customthe solvent was removed under vacuum
  8. customThe residue was purified by flash chromatography
  9. customIsolera® Purification System (0-40%, hexane-AcOEt)

出典と根拠

ORDレコード
ord-29a4e3914499492096d83fc6ec8fa133
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09388189B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート