Acetic Anhydride → methyl 6-[(4-fluorophenyl)methyl]-4-hydroxy-3,5-dioxo-7,8-dihydro-2H-2,6-naphthyridine-1-carboxylate

HRID 1817296노트

반응식

HRID 1817296 반응식
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:22])[CH:11]=[N+:12]([O-])[C:13]=3[C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:23])=[CH:4][CH:3]=1.C(OC(=O)C)(=[O:28])C.C[O-].[Na+]>>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:22])[C:11](=[O:28])[NH:12][C:13]=3[C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:23])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 7918Acetic AnhydrideHCID 10942334Sodium MethoxideHCID 69058416Methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

생성물 1

HCID 54692262methyl 6-[(4-fluorophenyl)methyl]-4-hydroxy-3,5-dioxo-7,8-dihydro-2H-2,6-naphthyridine-1-carboxylate

실험 절차

To methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide (0.178 g, 0.514 mmol) was added acetic anhydride (0.157 g, 1.542 mmol) and refluxed. After 1 hour, the reaction mixture was concentrated under vacuum, then sodium methoxide (30 wt. % in methanol, 0.083 g, 1.540 mmol) was added. After stirring at room temperature for 1 hour, the product mixture was concentrated under vacuum. The residue was purified by reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound as a pale yellow solid.

후처리

  1. temperaturerefluxed
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. concentrationthe product mixture was concentrated under vacuum
  4. customThe residue was purified by reverse phase HPLC
  5. washeluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA)

출처 및 근거

ORD 기록
ord-d9a42cfcda9c4bf4a04963e6c0bce904
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07598264B2

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