Methanesulfonic Acid → Garenoxacin mesylate hydrate

HRID 1018533Notes

Reaction equation

O.[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:19]4[CH:20]=[C:21]5[C:25](=[CH:26][CH:27]=4)[C@@H:24]([CH3:28])[NH:23][CH2:22]5)[C:13]=3[O:15][CH:16]([F:18])[F:17])[C:8](=[O:29])[C:7]([C:30]([OH:32])=[O:31])=[CH:6]2)[CH2:4][CH2:3]1.[CH3:33][S:34]([OH:37])(=[O:36])=[O:35]>C(O)C>[OH2:15].[CH3:33][S:34]([OH:37])(=[O:36])=[O:35].[CH:2]1([N:5]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:19]4[CH:20]=[C:21]5[C:25](=[CH:26][CH:27]=4)[C@@H:24]([CH3:28])[NH:23][CH2:22]5)[C:13]=3[O:15][CH:16]([F:18])[F:17])[C:8](=[O:29])[C:7]([C:30]([OH:32])=[O:31])=[CH:6]2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 40 °C

Procedure

In 192 ml of 50% ethanol is suspended 24 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid monohydrate, and the suspension is warmed to 40° C., after which 5.71 g of methanesulfonic acid is added to form a uniform solution. Subsequently, 2.4 g of activated carbon is added and the resulting mixture is stirred at the same temperature for 10 minutes, after which the insolubles are removed by filtration. The filtrate is concentrated and the crystals deposited are collected by filtration to obtain 26.64 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methanesulfonate monohydrate.

Workup

customto form a uniform solution
additionSubsequently, 2.4 g of activated carbon is added
customafter which the insolubles are removed by filtration
concentrationThe filtrate is concentrated
filtrationthe crystals deposited are collected by filtration

Sources & evidence

ORD record: ord-2aa49440462b4210bf4ef5f7edb667f9
Source dataset: uspto-grants-2002_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06482835B2

Reaction notes

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