Sodium Hydroxide → (S)-2,3-dihydroxypropyl 9-fluoro-3-methyl-10-(-4-methylpiperazin-1-yl)-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylate

HRID 1479222Notes

Reaction equation

FC(F)(F)C([O-])=O.[OH:8][CH:9]([CH2:37][OH:38])[CH2:10][O:11][C:12]([C:14]1[C:23](=[O:24])[C:22]2[C:17]3=[C:18]([O:33][CH2:34][C@H:35]([CH3:36])[N:16]3[CH:15]=1)[C:19]([N:26]1[CH2:31][CH2:30][NH+:29]([CH3:32])[CH2:28][CH2:27]1)=[C:20]([F:25])[CH:21]=2)=[O:13].[OH-].[Na+]>CO>[F:25][C:20]1[CH:21]=[C:22]2[C:17]3=[C:18]([O:33][CH2:34][CH:35]([CH3:36])[N:16]3[CH:15]=[C:14]([C:12]([O:11][CH2:10][C@@H:9]([OH:8])[CH2:37][OH:38])=[O:13])[C:23]2=[O:24])[C:19]=1[N:26]1[CH2:27][CH2:28][N:29]([CH3:32])[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 0 °C

Procedure

(S)-4-(6-((2,3-dihydroxypropoxy)carbonyl)-9-fluoro-3-methyl-7-oxo-3,7-dihydro-2H-[1,4]oxazino[2,3,4-ij]quinolin-10-yl)-1-methylpiperazin-1-ium 2,2,2-trifluoroacetate (0.50 g, 0.91 mmol) was dissolved in methanol under argon and cooled to 0° C. (ice/salt bath). 1 equiv. of NaOH dissolved in methanol (25 ml) was added slowly until the solution reached pH 7-pH 8. The reaction mixture was passed through a plug of Al2O3 (10% MeOH in CHCl3). The organic solvent was removed under reduced pressure giving a yellow solid (0.35 g, 88%)

Workup

additionwas added slowly until the solution
customThe organic solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-9bd494f59818432cbed96f07a877cbf6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09408919B2

Reaction notes

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