Sodium Hydroxide → HCID 19072250, compound

HRID 1955762Notes

Reaction equation

HRID 1955762 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]2[C:23]([O:24][CH3:25])=[C:22]3[C:17]([C:18](=[O:34])[C:19]([C:29]([O:31]CC)=[O:30])=[CH:20][N:21]3[CH:26]3[CH2:28][CH2:27]3)=[CH:16][C:15]=2[F:35])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[C:1]([O:5][C:6]([NH:8][C:9]1([C:14]2[C:23]([O:24][CH3:25])=[C:22]3[C:17]([C:18](=[O:34])[C:19]([C:29]([OH:31])=[O:30])=[CH:20][N:21]3[CH:26]3[CH2:27][CH2:28]3)=[CH:16][C:15]=2[F:35])[CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 19072249HCID 19072249, compound

Product 1

HCID 19072250HCID 19072250, compoundYield 101.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.3 g of ethyl 7-(1-t-butoxycarbonylaminocyclo-pentyl)-l-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate was suspended 40 ml of ethanol. Then 40 ml of a 1N aqueous solution of sodium hydroxide was added thereto and the resulting mixture was stirred at room temperature for 15 hours. After removing the solvent under reduced pressure, the mixture was acidified by adding methylene chloride and 2N HCl. The organic layer was collected, washed with water and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, 2.2 g of 7-(1-t-butoxycarbonylaminocyclopentyl)-1-cyclo-propyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecar-boxylic acid was obtained (yield: 100%).

Workup

  1. customAfter removing the solvent under reduced pressure
  2. additionby adding methylene chloride and 2N HCl
  3. customThe organic layer was collected
  4. washwashed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing the solvent under reduced pressure

Sources & evidence

ORD record
ord-a4f926e4247f43f0ac3638c52853bcf6
Source dataset
uspto-grants-1998_07
Patent number
US05776948

Reaction notes

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