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Dicyclohexylcarbodiimide → 1-[1-oxo-2-(4-Nitro-1H-imidazol-1-yl)octyl]-L-proline benzyl ester

HRID 375119
ノート
印刷プレビュー

反応式

HRID 375119 の反応式
C(N(C(C)C)CC)(C)C.Cl.[CH2:11]([O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][NH:21]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[N+:26]([C:29]1[N:30]=[CH:31][N:32]([CH:34]([CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:35](O)=[O:36])[CH:33]=1)([O-:28])=[O:27].OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.C(OCC)(=O)C>[CH2:11]([O:18][C:19](=[O:25])[C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:35](=[O:36])[CH:34]([N:32]1[CH:33]=[C:29]([N+:26]([O-:28])=[O:27])[N:30]=[CH:31]1)[CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 100836862-(4-nitro-1H-imidazol-1-yl)octanoic acidHCID 178418300HCID 178418300、化合物

生成物 1

HCID 537038381-[1-oxo-2-(4-Nitro-1H-imidazol-1-yl)octyl]-L-proline benzyl ester
収率 30.4%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Diisopropylethylamine (39.6 mmoles, 5.1 g) was added to a solution of L-proline benzyl ester hydrochloride (39.6 mmoles, 10.1 g) in 20 ml DMF at 0° and stirred for 1 hour. The solution was added to 2-(4-nitro-1H-imidazol-1-yl) octanoic acid (39.6 mmoles, 10.1 g) and hydroxybenzotriazole (43 mmoles, 5.8 g) in 10 ml DMF, and stirred for 30 minutes. Dicyclohexylcarbodiimide (43 mmoles, 8.97 g) was added portionwise over 2 hours. Ethyl acetate (50 ml) was added. The solution was filtered, dried over sodium sulfate and concentrated. The oil was chromatographed over silica gel eluted with 40% ethyl acetate in hexane to yield 5.32 g of 1-[1-oxo-2-(4-Nitro-1H-imidazol-1-yl)octyl]-L-proline benzyl ester.

後処理

  1. stirringstirred for 30 minutes
  2. filtrationThe solution was filtered
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe oil was chromatographed over silica gel
  6. washeluted with 40% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-b576186395aa42009b4de5c1a96d6ae1
出典データセット
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05484780

反応ノート

読み込み中…

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