Hydrochloric Acid → 5-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide

HRID 20750ノート

反応式

HRID 20750 の反応式
C(OC(=O)[NH:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([C:19](=[O:25])[NH:20][O:21][CH2:22][CH2:23][OH:24])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:15]([F:35])[C:14]=1[F:36])(C)(C)C.Cl.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:7][CH2:8][CH2:9][O:10]/[N:11]=[CH:12]/[C:13]1[C:14]([F:36])=[C:15]([F:35])[C:16]([NH:26][C:27]2[CH:32]=[CH:31][C:30]([I:33])=[CH:29][C:28]=2[F:34])=[C:17]([CH:18]=1)[C:19]([NH:20][O:21][CH2:22][CH2:23][OH:24])=[O:25]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 11445081HCID 11445081、化合物

生成物 1

HCID 113072055-[(E)-2-aminoethoxyiminomethyl]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)benzamide収率 37%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of {2-[2,3-difluoro-4-(2-fluoro-4-iodo-phenylamino)-5-(2-hydroxy-ethoxycarbamoyl)-benzylideneaminooxy]-ethyl}-carbamic acid tert-butyl ester (55 mg, 0.31 mmol) prepared in Step B in ethyl acetate (5 ml) was added 1 N HCl solution in ethyl acetate (1 ml), and the mixture was stirred at room temperature for 1.5 hours. After completion of the reaction, the reaction mixture was neutralized with saturated solution of sodium bicarbonate (50 ml), and extracted with ethyl acetate (3×100 ml). The extract was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure, and after washing with diethyl ether (10 ml), the residue was recrystallized from methanol to give (E)-5-[(2-amino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (17.31 mg, 37% yield) as a pale yellow solid.

後処理

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate (3×100 ml)
  3. washThe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure
  7. washafter washing with diethyl ether (10 ml)
  8. customthe residue was recrystallized from methanol

出典と根拠

ORDレコード
ord-9085666bbfa44ea5a6e6fce1e88ee452
出典データセット
uspto-grants-2010_06
特許番号
US07745663B2

反応ノート

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