(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 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 → (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 41819Notes

Reaction equation

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

Participants

Conditions

Temperature: 75 °C

Procedure

(S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 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 (5.67 g, 10.8 mmol) was dissolved in 80% aqueous acetic acid (45 mL). The reaction mixture was heated at 75° C. for 8 hrs. The solvent was removed under reduced pressure. Toluene was added to the residue and the solvent again removed under reduced pressure. The product was purified by column chromatography (10%, followed by 20%, 30%, and 75% methanol/chloroform as eluent) to give the title compound as an off-white solid in 84% yield.

Workup

customThe solvent was removed under reduced pressure
additionToluene was added to the residue
customthe solvent again removed under reduced pressure
customThe product was purified by column chromatography (10%, followed by 20%, 30%, and 75% methanol/chloroform as eluent)

Sources & evidence

ORD record: ord-bbafa3a7e96847efb03fa6e63bda8c6f
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08535655B2

Reaction notes

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