Methanesulfonic Acid → Garenoxacin mesylate hydrate

HRID 2222864Notes

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-quinoline-carboxylic 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-922c981b894248509e70ffb90576336c
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371868B2

Reaction notes

Loading…