Benzyl Bromide → Methyl 1-benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

HRID 1179325노트

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HRID 1179325 반응식
[Na].[OH:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][N:11]=2)[NH:6][C:5](=[O:13])[C:4]=1[C:14]([O:16][CH3:17])=[O:15].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.C(Cl)Cl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:18]([N:6]1[C:7]2[C:12](=[N:11][CH:10]=[CH:9][CH:8]=2)[C:3]([O:2][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]1=[O:13])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

7

반응물 3

HCID 7498Benzyl BromideHCID 5360545SodiumHCID 54729994Methyl 4-Hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

생성물 1

HCID 58977987Methyl 1-benzyl-4-(benzyloxy)-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
50 °C

실험 절차

To a solution of the sodium salt of methyl 4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate (2.0 g, 7.57 mmol) in water (50 mL) was added a solution of benzyl bromide (3.89 g, 22.72 mmol) in methylene chloride (50 mL). To the biphasic solution was then added tetrabutylammonium bromide (1.2 g, 3.79 mmol) and the reaction was sealed and heated to 50° C. After stirring overnight the reactions was cooled and the two layers were separated. The aqueous layer was extracted one time with methylene chloride and the combined organics were dried over sodium sulfate, filtered and concentrated. The crude mixture was separated by normal phase chromatography using an Isco 120 gram silica gel cartridge with a 50 minute gradient running at 40 mL/min. of 10% to 60% EtOAc/hexanes. The tubes containing the desired product were concentrated and taken on to the next step.

후처리

  1. temperaturewas cooled
  2. customthe two layers were separated
  3. extractionThe aqueous layer was extracted one time with methylene chloride
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was separated by normal phase chromatography
  8. customwith a 50 minute
  9. additionThe tubes containing the desired product
  10. concentrationwere concentrated

출처 및 근거

ORD 기록
ord-8d4c5bb30e484886b8afc49941b5e28c
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07279487B2

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