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

HRID 600876Notes

Reaction equation

HRID 600876 reaction equation
[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]

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6646bfaa0a824569ad17b1e6d5122c92
Source dataset
uspto-grants-2011_03
Patent number
US07902226B2

Reaction notes

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