Hydrochloric Acid → HCID 11794641, compound

HRID 1078272Notes

Reaction equation

HRID 1078272 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:13]2[CH2:17][C:16]([CH3:19])([CH3:18])[C@H:15]([NH:20]C(=O)C(F)(F)F)[CH2:14]2)[C:9]([CH3:27])=[C:8]2[C:3]=1[C:4](=[O:34])[C:5]([C:31]([OH:33])=[O:32])=[CH:6][N:7]2[CH:28]1[CH2:30][CH2:29]1.[OH-].[K+].Cl>O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([N:13]2[CH2:17][C:16]([CH3:19])([CH3:18])[C@H:15]([NH2:20])[CH2:14]2)[C:9]([CH3:27])=[C:8]2[C:3]=1[C:4](=[O:34])[C:5]([C:31]([OH:33])=[O:32])=[CH:6][N:7]2[CH:28]1[CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 10528859HCID 10528859, compound

Product 1

HCID 11794641HCID 11794641, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.47 g of 5-amino-1-cyclopropyl-7-((S)-4,4-dimethyl-3-trifluoroacetylamino-1-pyrrolidinyl)-6-fluoro-1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid, 0.32 g of potassium hydroxide and 3.2 ml of water was stirred at room temperature for 1 hour. The reaction mixture was neutralized with 10% hydrochloric acid to pH 8 and extracted with methylene chloride. The combined organic extracts were washed with water and brine, dried over sodium sulfate and evaporated. The residue was triturated with a mixture of acetone and diethyl ether to give 0.30 g of the desired compound as yellow crystals. The crystals were subsequently recrystallized from acetonitrile and 0.18 g of yellow needles, m.p. 191.5°-193° C. were obtained.

Workup

  1. extractionextracted with methylene chloride
  2. washThe combined organic extracts were washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was triturated with a mixture of acetone and diethyl ether

Sources & evidence

ORD record
ord-151776bfa53443df84536f75408c752d
Source dataset
uspto-grants-1996_08
Patent number
US05547962

Reaction notes

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