Tert-butyl 5-azaspiro[2.4]heptan-7-ylcarbamate → 7-(7-Tert-butoxycarbonylamino-5-azaspiro[2,4]heptan-5-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1721096Notes

Reaction equation

[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[CH:6]([C:17]([OH:19])=[O:18])[CH2:5]2)[CH2:3][CH2:2]1.[C:20]([O:24][C:25]([NH:27][CH:28]1[C:32]2([CH2:34][CH2:33]2)[CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>CS(C)=O>[C:20]([O:24][C:25]([NH:27][CH:28]1[C:32]2([CH2:33][CH2:34]2)[CH2:31][N:30]([C:11]2[CH:12]=[C:13]3[C:8]([C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:10]=2[F:15])[CH2:29]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 120 °C

Procedure

250 mg of 1-cyclopropyl-6,7-difluoro-2,3-dihydro-4-oxoquinoline-3-carboxylic acid and 250 mg of compound 11 were added to 4 ml of dimethyl sulfoxide and the mixture was heated at 120° C. for 2 hours. After cooling, the solvent was removed under reduced pressure and the residue was crystallized by the addition of ethanol. The crystals were collected by filtration. The procedure gave 7-(7-tert-butoxycarbonylamino-5-azaspiro[2.4]heptan-5-yl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid as a crude product.

Workup

temperatureAfter cooling
customthe solvent was removed under reduced pressure
customthe residue was crystallized by the addition of ethanol
filtrationThe crystals were collected by filtration

Sources & evidence

ORD record: ord-2d135255379140d0a5d583e1f314736b
Source dataset: uspto-grants-1996_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05508428

Reaction notes

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