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N-((Benzyloxy)carbonyl)-2-methylalanine → 2-(Carbobenzyloxy-alpha-methylalanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one

HRID 1900768
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HRID 1900768 반응식
[NH2:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3.[C:18]([NH:28][C:29]([CH3:34])([C:31](O)=[O:32])[CH3:30])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].CCN=C=NCCCN(C)C.Cl>CN(C)C=O.N1C=CC=CC=1>[C:18]([NH:28][C:29]([CH3:34])([C:31]([NH:1][CH2:2][CH:3]1[O:17][C:6]2=[C:7]3[C:12](=[C:13]([CH3:15])[CH:14]=[C:5]2[CH2:4]1)[NH:11][C:10](=[O:16])[CH:9]=[CH:8]3)=[O:32])[CH3:30])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]
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참가 물질

6

반응물 3

HCID 294936N-((Benzyloxy)carbonyl)-2-methylalanineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 233695672-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one

생성물 1

HCID 867499942-(Carbobenzyloxy-alpha-methylalanyl]aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one수율 43.6%

시약·촉매·용매 2

HCID 1049
Pyridine
용매
HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

2-Aminomethyl-5-methyl-2,3,6,7-tetrahydrofuro-[2,3-f]quinoline-7-one (3.00 g, 13.0 mmol) was dissolved in a solvent mixture of dimethylformamide (200 ml) and pyridine (100 ml). To this solution, N-carbobenzyloxy-α-methylalanine (4.64 g, 19.5 mmol) and WSC-HCl (3.48 g, 19.5 mmol) were added and the mixture was stirred at 50° C. for 48 hours. The reaction mixture was condensed under reduced pressure, and the residue was subjected to extraction using a solvent mixture (chloroform--methanol =4:1) combined with 1N-HCl. The organic phase was washed with saturated aqueous NaCl solution, followed by drying and condensing under reduced pressure. The resultant residue was purified by silica gel column chromatography (chloroform: methanol=25:1). The crude crystals were subjected to a recrystallizing procedure from chloroform--methanol. As a result, 2.55 g of the title compound was obtained as colorless powdery crystals (43.7%).

후처리

  1. customcondensed under reduced pressure
  2. extractionthe residue was subjected to extraction
  3. washThe organic phase was washed with saturated aqueous NaCl solution
  4. customby drying
  5. customcondensing under reduced pressure
  6. customThe resultant residue was purified by silica gel column chromatography (chloroform: methanol=25:1)

출처 및 근거

ORD 기록
ord-27a829dd020f4c6da72e7f15e4fc3c48
출처 데이터셋
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05576324

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