HCID 68647637, compound → 3-[2-Chloro-4-(2-methoxy-2-oxoethyl)phenyl]-5-methyl-1,2-oxazole-4-carboxylic acid

HRID 1162516Notes

Reaction equation

HRID 1162516 reaction equation
C([O:5][C:6]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[Cl:25])=[N:10][O:11][C:12]=1[CH3:13])=[O:7])(C)(C)C>FC(F)(F)C(O)=O>[Cl:25][C:15]1[CH:16]=[C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH:18]=[CH:19][C:14]=1[C:9]1[C:8]([C:6]([OH:7])=[O:5])=[C:12]([CH3:13])[O:11][N:10]=1

Participants

3

Reactant 1

HCID 68647637HCID 68647637, compound

Product 1

HCID 451231353-[2-Chloro-4-(2-methoxy-2-oxoethyl)phenyl]-5-methyl-1,2-oxazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

3-(2-chloro-4-methoxycarbonylmethyl-phenyl)-5-methyl-isoxazole-4-carboxylic acid tert-butyl ester 24 (1.0 g, 2.7 mmol) is dissolved in trifluoroacetic acid (20 mL) and stirred at room temperature for 4 hours. Then the solvent is evaporated and the remainder is dried on high vacuum to afford 3-(2-Chloro-4-methoxycarbonylmethyl-phenyl)-5-methyl-isoxazole-4-carboxylic acid 25 as a white solid: 1H-NMR (400 MHz, CDCl3) δ=10.36 (s, 1H), 7.42 (s, 1H), 7.36 (d, J=7.8 Hz, 1H), 7.27 (dd, J=8.4 Hz, J=0.6 Hz, 1H), 3.74 (s, 3H), 3.68 (s, 2H), 2.78 (s, 3H). MS calculated for C14H13ClNO5 (M+H+) 310.0, found 310.3.

Workup

  1. customThen the solvent is evaporated
  2. customthe remainder is dried on high vacuum

Sources & evidence

ORD record
ord-da62f113aa9c42e1bf524dff955524da
Source dataset
uspto-grants-2010_10
Patent number
US07820705B2

Reaction notes

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