Dimethylformamide → HCID 136202024, compound

HRID 2075972Notes

Reaction equation

[OH:1][C:2]1[C:3]([N+:19]([O-:21])=[O:20])=[C:4]([C:9]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)=[CH:10][C:11]=1[OH:12])[C:5]([O:7][CH3:8])=[O:6].[C:22](Cl)(=[O:26])[O:23][CH2:24][CH3:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)(=O)C.O>[CH2:24]([O:23][C:22]([O:12][C:11]1[CH:10]=[C:9]([C:13]2[N:17]=[C:16]([CH3:18])[O:15][N:14]=2)[C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]([N+:19]([O-:21])=[O:20])[C:2]=1[OH:1])=[O:26])[CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of methyl 3,4-dihydroxy-6-(5-methyl-[1,2,4]-oxadiazol-3-yl)-2-nitrobenzoate (compound 1-5) (50 mg), ethyl chlorocarbonate (0.02 mL), potassium carbonate (28 mg) and N,N-dimethylformamide (2 mL) was stirred at 50° C. for 3 hours. After cooling to room temperature, water and ethyl acetate were added to the mixture. The separated organic layer was washed with water and brine successively, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: 20%-100% ethyl acetate/hexane, gradient elution) to give the title compound (51 mg). The structural formula was illustrated in table 13.

Workup

temperatureAfter cooling to room temperature
washThe separated organic layer was washed with water and brine successively
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: 20%-100% ethyl acetate/hexane, gradient elution)

Sources & evidence

ORD record: ord-15a76580e71a468d92d8f8d10c580c37
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923462B2

Reaction notes

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