HCID 57758693, Verbindung → HCID 15604366, Verbindung

HRID 1510346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510346
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

Komponenten

3

Edukt 1

HCID 57758693HCID 57758693, Verbindung

Produkt 1

HCID 15604366HCID 15604366, VerbindungAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-25748264c7f1412eaee196d393a0ffe9
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211910B2

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