Hydrochloric Acid → 6,7-difluoro-1,4-dihydro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acid

HRID 2183685ノート

反応式

HRID 2183685 の反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([C@@H:15]1[CH2:17][C@@H:16]1[F:18])[CH:7]=[C:6]([C:19]([O:21]CC)=[O:20])[C:5]2=[O:24].Cl>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:13][CH3:14])[C:11]=1[F:12])[N:8]([C@@H:15]1[CH2:17][C@@H:16]1[F:18])[CH:7]=[C:6]([C:19]([OH:21])=[O:20])[C:5]2=[O:24]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 60004315ethyl 6,7-difluoro-1-[(1R, 2S)-2-fluoro-1-cyclopropyl]-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate

生成物 1

HCID 120946186,7-difluoro-1,4-dihydro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-4-oxo-3-quinolinecarboxylic acid収率 96.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of ethyl 6,7-difluoro-1-[(1R, 2S)-2-fluoro-1-cyclopropyl]-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (120.8 g; 354.1 mmol), glacial acetic acid (210 ml), and conc. hydrochloric acid (420 ml) was refluxed for 6 hours, followed by cooling. The cooled reaction mixture was poured into ice/water (1500 ml) while being stirred, and the mixture was stirred for an additional 30 minutes at room temperature. Crystals precipitated were collected by filtration, and the crystals were sequentially washed with an excessive amount of purified water, ethanol (300 ml), and diethyl ether (500 ml). The crystals were purified through recrystallization from ethanol-acetone (also through treatment with activated carbon and filtration), followed by drying under reduced pressure at 70° C., to thereby yield 107.0 g of the title compound as white needles (yield: 96.5%).

後処理

  1. temperaturewas refluxed for 6 hours
  2. temperatureby cooling
  3. customThe cooled reaction mixture
  4. stirringthe mixture was stirred for an additional 30 minutes at room temperature
  5. customCrystals precipitated
  6. filtrationwere collected by filtration
  7. washthe crystals were sequentially washed with an excessive amount of purified water, ethanol (300 ml), and diethyl ether (500 ml)
  8. customThe crystals were purified through recrystallization from ethanol-acetone (also through treatment
  9. filtrationwith activated carbon and filtration),
  10. customby drying under reduced pressure at 70° C.

出典と根拠

ORDレコード
ord-b8f7972cb7e046ff8f5315c029835cdb
出典データセット
uspto-grants-2005_05
特許番号
US06900225B2

反応ノート

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