Trifluoroacetic acid → Methyl 2-(3-(dimethylcarbamoyl)-4-nitrophenyl)acetate

HRID 494390Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=1)C(OC(C)(C)C)=O.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[C:14]([C:21](=[O:25])[N:22]([CH3:24])[CH3:23])[CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The 2-(3-dimethylcarbamoyl-4-nitrophenyl)malonic acid tert-butyl ester methyl ester (1.22 g) obtained in Example 2b) was dissolved in dichloromethane (10 mL), and the solution was cooled to 0° C. After addition of trifluoroacetic acid (10 mL), the mixture was stirred at room temperature for 6 hours, and concentrated, followed by azeotropic distillation with toluene. The residue was purified by column chromatography on silica gel with ethyl acetate:hexane=3:1 to give the title compound (712 mg).

Workup

concentrationconcentrated
distillationfollowed by azeotropic distillation with toluene
customThe residue was purified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record: ord-82bd61dfd8e344c5b49681ce50dda503
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538140B2

Reaction notes

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