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

HRID 1817296ノート

反応式

HRID 1817296 の反応式
[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

参加物

4

反応物 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

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d9a42cfcda9c4bf4a04963e6c0bce904
出典データセット
uspto-grants-2009_10
特許番号
US07598264B2

反応ノート

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