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

HRID 600876노트

반응식

HRID 600876 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6646bfaa0a824569ad17b1e6d5122c92
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902226B2

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