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

HRID 1609765
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HRID 1609765 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

Diisopropylethylamine (39.6 mmoles, 5.1 g) was added to a solution of L-proline benzyl ester hydrochloride (39.6 moles, 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.

후처리

  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

출처 및 근거

ORD 기록
ord-961bedeac5654cba89b08f8293bb9c66
출처 데이터셋
uspto-grants-1995_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05401851

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