Methanesulfonic Acid → HCID 178511751, compound

HRID 278398Notes

Reaction equation

CS(O)(=O)=O.CS(O)(=O)=O.[CH2:11]1[N:17]([C:18]2[N:28]=[C:27]3[C:21]([C:22]([C:24]([C:37]([OH:39])=[O:38])=[CH:25][N:26]3[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])=[O:23])=[CH:20][C:19]=2[F:40])[CH2:16][C@@H:13]2[CH:14]([NH2:15])[C@H:12]12>>[CH:33]1[C:32]([F:35])=[CH:31][C:30]([F:36])=[C:29]([N:26]2[C:27]3=[N:28][C:18]([N:17]4[CH2:11][C@@H:12]5[C@@H:14]([NH2:15])[C@@H:13]5[CH2:16]4)=[C:19]([F:40])[CH:20]=[C:21]3[C:22](=[O:23])[C:24]([C:37]([OH:39])=[O:38])=[CH:25]2)[CH:34]=1

Participants

Reactant 2

HCID 6395Methanesulfonic Acid

HCID 62960147059-75-4

Product 1

HCID 178511751HCID 178511751, compound

Conditions

Temperature: 45 °C

Procedure

Tetrahydrofuran (250 cm3), ethyl (1α,5α,6α)-7-(6-benzylidenylamino-3-azabicyclo[3.1.0]hex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (25.05 g, 47 mmol) obtained above, and water (250 cm3) were treated with 97% methanesulfonic acid (13.3 g, 138 mmol) and heated to reflux for 24 h. The resulting solution, which contained trovafloxacin methanesulfonate salt, was cooled to 45° C., treated with activated carbon (2.5 g) for 1 hr and filtered. Treatment of the filtrate with saturated aqueous sodium bicarbonate to pH 8 (see PCT Publication No. WO 97/07800, example 1A) yields the above-titled compound.

Workup

temperatureheated
temperatureto reflux for 24 h
additiontreated with activated carbon (2.5 g) for 1 hr
filtrationfiltered

Sources & evidence

ORD record: ord-f2f4de15c96e4d44bd3b2d1070a32678
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06359137B1

Reaction notes

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