Acetic Acid → 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-Carboxylic Acid

HRID 600876ノート

反応式

HRID 600876 の反応式
[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([O:13][CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([O:21]CC)=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18].C(O)(=O)C.Cl>O>[NH2:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([O:13][CH3:14])=[C:8]2[C:3]=1[C:4](=[O:24])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[C@@H:15]1[CH2:17][C@@H:16]1[F:18]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 67271608ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate

生成物 1

HCID 672722805-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-Carboxylic Acid収率 51.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of ethyl 5-amino-7-fluoro-1-[2-(S)-fluoro-1-(R)-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate (2.68 g, 7.92 mmol), acetic acid (20 ml) and concentrated hydrochloric acid (20 ml) was heated under reflux for 3 hours. After cooling there action solution with ice, water (200 ml) was poured therein and the precipitated crystals were filtered out. After washing with excess water, a small amount of cold ethanol and excess diethyl ether in that order, the crude crystals obtained were purified by recrystallization in a mixed solvent of chloroform/methanol and then dried under a reduced pressure. 1.26 g (51%) of the title compound was thereby obtained in the form of yellow crystals.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. additionwas poured
  4. filtrationthe precipitated crystals were filtered out
  5. washAfter washing with excess water
  6. customa small amount of cold ethanol and excess diethyl ether in that order, the crude crystals obtained
  7. customwere purified by recrystallization in a mixed solvent of chloroform/methanol
  8. customdried under a reduced pressure

出典と根拠

ORDレコード
ord-6646bfaa0a824569ad17b1e6d5122c92
出典データセット
uspto-grants-2011_03
特許番号
US07902226B2

反応ノート

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