HCID 57758693, compound → HCID 15604366, compound

HRID 229512Notes

Reaction equation

HRID 229512 reaction equation
C(OC([NH:8][C:9]1([CH3:37])[C:13]2([CH2:15][CH2:14]2)[CH2:12][N:11]([C:16]2[C:25]([O:26][CH3:27])=[C:24]3[C:19]([C:20](=[O:35])[C:21]([C:32]([OH:34])=[O:33])=[CH:22][N:23]3[C@@H:28]3[CH2:30][C@@H:29]3[F:31])=[CH:18][C:17]=2[F:36])[CH2:10]1)=O)(C)(C)C>Cl>[NH2:8][C:9]1([CH3:37])[C:13]2([CH2:14][CH2:15]2)[CH2:12][N:11]([C:16]2[C:25]([O:26][CH3:27])=[C:24]3[C:19]([C:20](=[O:35])[C:21]([C:32]([OH:34])=[O:33])=[CH:22][N:23]3[C@@H:28]3[CH2:30][C@@H:29]3[F:31])=[CH:18][C:17]=2[F:36])[CH2:10]1

Participants

3

Reactant 1

HCID 57758693HCID 57758693, compound

Product 1

HCID 15604366HCID 15604366, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

The 7-[7-(tert-butoxycarbonylamino)-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid produced in Reference Example 29 (870 mg, 1.676 mmol) was dissolved in concentrated hydrochloric acid (10 mL) in an ice bath, and the mixture was stirred at room temperature for 20 minutes and washed chloroform (20 mL×5). Saturated aqueous solution of sodium hydroxide was added to the aqueous layer in an ice bath to adjust the pH to 12.0, and the pH was further adjusted to 7.4 by adding hydrochloric acid. The solution was extracted with a mixed solution (chloroform:methanol, 10:1) (200 mL×2), and then, with lower layer of a mixed solution (200 mL) (chloroform:methanol:water, 7:3:1). The organic layers were combined and dried with anhydrous sodium sulfate, and the solvent was removed by distillation. The residue was purified by recrystallization from ethanol, and the crystals were dried under reduced pressure to obtain 644 mg (1.535 mmol, 92%) of the title compound as a pale pink powder.

Workup

  1. washwashed chloroform (20 mL×5)
  2. additionSaturated aqueous solution of sodium hydroxide was added to the aqueous layer in an ice bath
  3. additionby adding hydrochloric acid
  4. extractionThe solution was extracted with a mixed solution (chloroform:methanol, 10:1) (200 mL×2)
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was removed by distillation
  7. customThe residue was purified by recrystallization from ethanol
  8. customthe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-ed2e80cbcbf84f57bfc5a9db402118b1
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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