Water → HCID 68991589, compound

HRID 240784Notes

Reaction equation

[CH3:1][N:2]([CH3:18])[CH2:3][C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]#[CH:17])[CH:14]=2)[NH:9][N:8]=1)=[O:5].[N:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)=[N+:20]=[N-:21].O.O[C@H]([C@@H]1C([O-])=C(O)C(=O)O1)CO.[Na+]>C(O)(C)(C)C.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH3:1][N:2]([CH3:18])[CH2:3][C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:16]3[N:21]=[N:20][N:19]([CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=4)[CH:17]=3)[CH:14]=2)[NH:9][N:8]=1)=[O:5]

Participants

Conditions

Temperature: 60 °C

Procedure

To a suspension of Example 282E (0.16 g, 0.660 mmol) in tert-butanol (1.2 mL) was added 1-(azidomethyl)-3-methylbenzene (0.098 g, 0.667 mmol), then water (1.2 mL). A solution of sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (0.057 mL, 0.066 mmol, 1.6 M in water) and an aqueous solution of copper (II) sulfate pentahydrate (0.019 mL, 6.6 μmol, 0.34M) was added. The reaction mixture was heated at about 60° C. for about 2 hours. The solvent was removed under reduced pressure and the residue was purified by reverse phase HPLC using acetonitrile/water (0.05 M ammonium acetate) gradient elution method to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.77 (s, 1H), 10.05 (s, 1H), 8.56 (s, 1H), 8.24 (s, 1H), 7.82 (d, 1H, J=8.6), 7.50 (d, 1H, J=8.8), 7.28 (t, 1H, J=7.6), 7.16 (m, 4H), 5.59 (s, 2H), 3.18 (s, 2H), 2.34 (s, 6H), 2.30 (s, 3H). MS (ESI+) m/z 390.3 (M+H)+.

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by reverse phase
washacetonitrile/water (0.05 M ammonium acetate) gradient elution method

Sources & evidence

ORD record: ord-e28e87a39a224d9eb81329e911a97348
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08648069B2

Reaction notes

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