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Morpholine → 3-nitro-4-valeramidobenzoic Acid Morpholide

HRID 1939288
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HRID 1939288 반응식
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([OH:9])=O)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[NH:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1>O1CCCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[NH:13][C:14](=[O:19])[CH2:15][CH2:16][CH2:17][CH3:18])[C:7]([N:45]1[CH2:50][CH2:49][O:48][CH2:47][CH2:46]1)=[O:9])([O-:3])=[O:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8083MorpholineHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 117776583-nitro-4-(pentanoylamino)benzoic Acid

생성물 1

HCID 538887563-nitro-4-valeramidobenzoic Acid Morpholide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In tetrahydrofuran (800 ml), 3 -nitro-4-valeramidobenzoic acid ([1]-(11)-1) (20.0 g) was dissolved. Dicyclohexylcarbodiimide (17.1 g) and 1-hydroxybenzotriazole (11.2 g) were added to the solution, and the mixture was stirred at room temperature for 15 minutes. Morpholine (7.27 g) was further added to the solution. The mixture was stirred for 16 hours. After the insolubles were removed from the reaction solution, the solution was concentrated and dried. The crude product was dissolved in chloroform, and the insolubles were removed, and the solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1) to obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals.

후처리

  1. stirringThe mixture was stirred for 16 hours
  2. customAfter the insolubles were removed from the reaction solution
  3. concentrationthe solution was concentrated
  4. customdried
  5. dissolutionThe crude product was dissolved in chloroform
  6. customthe insolubles were removed
  7. customthe solution was purified by silica gel column chromatography (Kieselgel 60=400 g, chloroform/methanol=30/1)
  8. customto obtain the compound ([1]-(12)-1) (22.95 g) as yellow needle crystals

출처 및 근거

ORD 기록
ord-b6bb95ed191a4ecb8596110a2b2d0650
출처 데이터셋
uspto-grants-1997_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05696118

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