HCID 57758731, compound → HCID 15604332, compound

HRID 229522Notes

Reaction equation

HRID 229522 reaction equation
C(OC([NH:8][C:9]1([CH3:35])[C:13]2([CH2:15][CH2:14]2)[CH2:12][N:11]([C:16]2[C:17]([F:34])=[CH:18][C:19]3[C:29](=[O:30])[C:28]([C:31]([OH:33])=[O:32])=[CH:27][N:21]4[C@@H:22]([CH3:26])[CH2:23][O:24][C:25]=2[C:20]=34)[CH2:10]1)=O)(C)(C)C>Cl>[NH2:8][C:9]1([CH3:35])[C:13]2([CH2:15][CH2:14]2)[CH2:12][N:11]([C:16]2[C:17]([F:34])=[CH:18][C:19]3[C:29](=[O:30])[C:28]([C:31]([OH:33])=[O:32])=[CH:27][N:21]4[C@@H:22]([CH3:26])[CH2:23][O:24][C:25]=2[C:20]=34)[CH2:10]1

Participants

3

Reactant 1

HCID 57758731HCID 57758731, compound

Product 1

HCID 15604332HCID 15604332, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

(3S)-10-[7-(tert-butoxycarbonylamino)-7-methyl-5-azaspiro[2.4]heptane-5-yl]-9-fluoro-2,3-dihydro-3-methyl-7-oxo-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acid (761 mg, 1.56 mmol) was dissolved in concentrated hydrochloric acid (6.5 mL) in an ice bath, and the mixture was stirred at room temperature for 120 minutes. The reaction mixture was washed with chloroform, and saturated aqueous solution of sodium hydroxide was added to the aqueous layer in an ice bath to a pH of 12.0. Hydrochloric acid was then added to adjust pH to 7.4, and the solution was extracted with lower layer of a mixed solution (chloroform:methanol:water, 7:3:1). After combining the organic layers, and drying with anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure. Chloroform was added to the residue, and the insoluble content was removed by filtration. The filtrate distilled under reduced pressure. The residue was purified by crystallization from ethanol, and dried under reduced pressure to obtain 260 mg (0.68 mmol, 43%) of the title compound as a yellow powder.

Workup

  1. washThe reaction mixture was washed with chloroform, and saturated aqueous solution of sodium hydroxide
  2. additionwas added to the aqueous layer in an ice bath to a pH of 12.0
  3. additionHydrochloric acid was then added
  4. extractionthe solution was extracted with lower layer of a mixed solution (chloroform:methanol:water, 7:3:1)
  5. dry with materialdrying with anhydrous sodium sulfate
  6. customthe solvent was removed by distillation under reduced pressure
  7. additionChloroform was added to the residue
  8. customthe insoluble content was removed by filtration
  9. distillationThe filtrate distilled under reduced pressure
  10. customThe residue was purified by crystallization from ethanol
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-d5a66445e8954084a938089162052284
Source dataset
uspto-grants-2009_07
Patent number
US07563805B2

Reaction notes

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