Methyl iodide → HCID 69058481、化合物

HRID 1817332ノート

反応式

HRID 1817332 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:12]([C:16]([O:18][CH3:19])=[O:17])=[N:11][C:10]([OH:20])=[C:9]([OH:21])[C:8]=2[C:7]1=[O:22].[CH3:27][O-].C[O-].[Mg+2].IC>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[F:26])[CH2:5][N:6]1[CH2:15][CH2:14][C:13]2[C:8](=[C:9]([OH:21])[C:10](=[O:20])[N:11]([CH3:27])[C:12]=2[C:16]([O:18][CH3:19])=[O:17])[C:7]1=[O:22]

参加物

5

反応物 3

HCID 6328Methyl iodide2 回HCID 164537Methanol, magnesium salt (2:1)HCID 178499134HCID 178499134、化合物

生成物 1

HCID 69058481HCID 69058481、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
45 °C

実験手順

To a solution of methyl 6-(3-chloro-4-fluorobenzyl)-3,4-dihydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (18.00 g, 47 mmol) in DMF (200 mL) was added magnesium methylate (96.08 mL, 95 mmol), and the reaction was warmed for 1 hour and cooled. The reaction was treated with iodomethane (17.66 mL, 283 mmol) and stirred at 45° C. overnight. At this time, LCMS showed the reaction incomplete, and an additional equivalent of iodomethane (2.95 mL, 48 mmol) was added. The reaction was again stirred for 4 hours. The solvent was removed in vacuo, and the resulting oil was partitioned between chloroform and 1N HCl. The aqueous layer was washed twice more with chloroform. The organic fractions were extracted with 10% sodium bisulfite, and the bisulfite layer was washed twice with chloroform. The combined organic layers were washed with 5% aqueous HCl and brine, dried over sodium sulfate and concentrated in vacuo to afford the product as a black oil. This material appears quite clean by NMR and HPLC, but is highly colored.

後処理

  1. temperaturethe reaction was warmed for 1 hour
  2. temperaturecooled
  3. additionwas added
  4. stirringThe reaction was again stirred for 4 hours
  5. customThe solvent was removed in vacuo
  6. customthe resulting oil was partitioned between chloroform and 1N HCl
  7. washThe aqueous layer was washed twice more with chloroform
  8. extractionThe organic fractions were extracted with 10% sodium bisulfite
  9. washthe bisulfite layer was washed twice with chloroform
  10. washThe combined organic layers were washed with 5% aqueous HCl and brine
  11. dry with materialdried over sodium sulfate
  12. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-3dc73c1fd1c94fe6b55769fe2911918e
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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