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

HRID 1267614Notes

Reaction equation

HRID 1267614 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[C:28]([F:29])=[C:27]4[C:22]([C:23](=[O:36])[C:24]([C:33]([OH:35])=[O:34])=[CH:25][N:26]4[CH:30]4[CH2:32][CH2:31]4)=[CH:21][C:20]=3[F:37])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(OCC)C>ClCCl>[CH:30]1([N:26]2[C:27]3[C:22](=[CH:21][C:20]([F:37])=[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)[C:28]=3[F:29])[C:23](=[O:36])[C:24]([C:33]([OH:35])=[O:34])=[CH:25]2)[CH2:31][CH2:32]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 865847337-[2-(t-Butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 544359131-Cyclopropyl-6,8-difluoro-7-[8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-4-oxo-1,4-dihydro-3-quinolinecarboxylic acidYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7-[2-(t-butoxycarbonyl)-8-(methoxyimino)-2,6-diazaspiro[3,4]oct-6-yl]-1-cyclopropyl-6,8-difluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid was dissolved in 5 ml of dichloromethane and thereto 1ml of trifluoroacetic acid was added dropwise. The mixture was stirred for 5 hours at room temperature and thereto 10 ml of ethylether was added. It was additionally stirred for 1 hour, and thus precipitated solid was filtered and dried. Thus obtained solid was dissolved in 5 ml of diluted sodium hydroxide and neutralized with diluted hydrochloric acid. The resulting precipitate was filtered and dried to give 115 mg of the titled compound (yield: 87.4%).

Workup

  1. stirringIt was additionally stirred for 1 hour
  2. filtrationthus precipitated solid was filtered
  3. customdried
  4. dissolutionThus obtained solid was dissolved in 5 ml of diluted sodium hydroxide and neutralized with diluted hydrochloric acid
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-202379544ef649cab86be840ca0c513a
Source dataset
uspto-grants-2003_04
Patent number
US06552196B2

Reaction notes

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