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

HRID 2038626ノート

反応式

HRID 2038626 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-27617004e4fc4f469f81a0f58d64ec34
出典データセット
uspto-grants-2013_11
特許番号
US08575391B2

反応ノート

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