Hydrogen Peroxide → Methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate 2-oxide

HRID 1817295Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:13]([C:17]([O:19][CH3:20])=[O:18])=[N:12][CH:11]=[C:10]([OH:21])[C:9]=3[C:8]2=[O:22])=[CH:4][CH:3]=1.[OH:25]O>C(O)(=O)C>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][N:7]2[CH2:16][CH2:15][C:14]3[C:9](=[C:10]([OH:21])[CH:11]=[N+:12]([O-:25])[C:13]=3[C:17]([O:19][CH3:20])=[O:18])[C:8]2=[O:22])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 6-(4-fluorobenzyl)-4-hydroxy-5-oxo-5,6,7,8-tetrahydro-2,6-naphthyridine-1-carboxylate (0.509 g, 1.541 mmol) in acetic acid (2 mL) was added hydrogen peroxide (35% wt % in H2O, 0.262 g, 7.705 mmol). The reaction mixture was heated to 100° C. for 1 hour. The product mixture was concentrated under vacuum and purified by reverse phase HPLC eluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA) to afford the title compound as a yellow solid.

Workup

concentrationThe product mixture was concentrated under vacuum
custompurified by reverse phase HPLC
washeluting with 5%-95% acetonitrile (0.1% TFA) in H2O (0.1% TFA)

Sources & evidence

ORD record: ord-0763d17dd36c4028ac0e67f6c4fa670c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598264B2

Reaction notes

Loading…