Diethyl Ether → 1-Cyclopropyl-6-fluoro-7-[8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methane sulfonate

HRID 1267613Notes

Reaction equation

HRID 1267613 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([C:15](=[N:16][O:17][CH3:18])[CH2:14][N:13]([C:19]3[CH:28]=[C:27]4[C:22]([C:23](=[O:35])[C:24]([C:32]([OH:34])=[O:33])=[CH:25][N:26]4[CH:29]4[CH2:31][CH2:30]4)=[CH:21][C:20]=3[F:36])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)C.[CH3:49][S:50]([OH:53])(=[O:52])=[O:51]>ClCCl.C(O)C>[CH3:49][S:50]([OH:53])(=[O:52])=[O:51].[CH:29]1([N:26]2[C:27]3[C:22](=[CH:21][C:20]([F:36])=[C:19]([N:13]4[CH2:14][C:15](=[N:16][O:17][CH3:18])[C:10]5([CH2:11][NH:8][CH2:9]5)[CH2:12]4)[CH:28]=3)[C:23](=[O:35])[C:24]([C:32]([OH:34])=[O:33])=[CH:25]2)[CH2:30][CH2:31]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 6422Trifluoroacetic acidHCID 865847327-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 881031311-Cyclopropyl-6-fluoro-7-[8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methane sulfonateYield 28.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

7-[2-(t-butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclo propyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolincarboxylic acid was dissolved in 5 ml of dichloromethane and thereto 1 ml of trifluoroacetic acid was added by dropping. The resulting mixture was stirred at room temperature for 18 hours, and thereto 10 ml of ethylether was added. The resulting precipitate was filtered and dried. Thus obtained solid was dissolved in 2 ml of diluted NaOH and neutralized with diluted hydrochloric acid, and the resulting precipitate was filtered and dried. The solid thus obtained was added to 2 ml of 1N-methanesulfonic acid in ethanol and stirred at room temperature for 3 hours. The precipitate was filtered and dried to give 35 mg of the titled compound (yield: 28.5%).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. customdried
  3. dissolutionThus obtained solid was dissolved in 2 ml of diluted NaOH and neutralized with diluted hydrochloric acid
  4. filtrationthe resulting precipitate was filtered
  5. customdried
  6. customThe solid thus obtained
  7. stirringstirred at room temperature for 3 hours
  8. filtrationThe precipitate was filtered
  9. customdried

Sources & evidence

ORD record
ord-bab81d6078ec4c2982d9ed893792754f
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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