1-Cyclopropyl-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid → E 4441

HRID 1651394Notes

Reaction equation

HRID 1651394 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:27])=[C:11]([N:15]4[CH2:18][C:17]([CH3:26])([NH:19]C(=O)C(F)(F)F)[CH2:16]4)[C:12]=3[F:14])[C:7](=[O:28])[C:6]([C:29]([OH:31])=[O:30])=[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:27])=[C:11]([N:15]4[CH2:16][C:17]([CH3:26])([NH2:19])[CH2:18]4)[C:12]=3[F:14])[C:7](=[O:28])[C:6]([C:29]([OH:31])=[O:30])=[CH:5]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 230517821-Cyclopropyl-6,8-difluoro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 130229E 4441Yield 55.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 0.8 g (1.8 mmoles) of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-3-trifluoroacetamido-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid (example 11) in a mixture of 10 ml of 1N sodium hydroxide and 2 ml of ethanol is refluxed for 3 hours. It is evaporated under vacuum and acetic acid is added. The product is filtered and washed with water and ethanol. 0.35 g (55%) of 1-cyclopropyl-6,8-difluoro-1,4-dihydro-7-(3-methyl-3-amino-1-azetidinyl)-4-oxo-3-quinolinecarboxylic acid are obtained having a melting point of 298°-300° C.

Workup

  1. temperatureis refluxed for 3 hours
  2. customIt is evaporated under vacuum and acetic acid
  3. additionis added
  4. filtrationThe product is filtered
  5. washwashed with water and ethanol

Sources & evidence

ORD record
ord-c6a0e8f7c3574b22b91f3ce453c9db8c
Source dataset
uspto-grants-1990_05
Patent number
US04927926

Reaction notes

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