Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate → 1-Cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

HRID 1651391Notes

Reaction equation

HRID 1651391 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:24])=[C:11]([N:15]4[CH2:18][CH:17]([O:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:25])[C:6]([C:26]([O:28]CC)=[O:27])=[CH:5]2)[CH2:3][CH2:2]1>[OH-].[Na+].C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:24])=[C:11]([N:15]4[CH2:16][CH:17]([O:19][S:20]([CH3:23])(=[O:21])=[O:22])[CH2:18]4)[C:12]=3[F:14])[C:7](=[O:25])[C:6]([C:26]([OH:28])=[O:27])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 15615454Ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 100932021-Cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.2 g (0.4 mmole) of ethyl 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylate (example 3) in 6 ml of 0.5N sodium hydroxide and 1 ml of ethanol is refluxed for 1 hour. It is evaporated under vacuum, and acetic acid is added. Filtering and washing yield 0.18 g (96%) of 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 240°-4° C.

Workup

  1. customIt is evaporated under vacuum, and acetic acid
  2. additionis added
  3. filtrationFiltering
  4. washwashing yield 0.18 g (96%) of 1-cyclopropyl-6,8-difluoro-7-(3-mesyloxy-1-azetidinyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid melting at 240°-4° C.

Sources & evidence

ORD record
ord-768a549440c0465f8abb87e6081959b6
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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