Potassium Carbonate → 1-(2-Tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

HRID 917724Notes

Reaction equation

HRID 917724 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:10]([C:24]([O:26]CC)=[O:25])=[CH:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CCO.Cl>[C:1]([O:5][C:6](=[O:29])[CH2:7][N:8]1[C:13](=[O:14])[CH:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([I:22])=[CH:18][C:17]=2[F:23])[C:10]([C:24]([OH:26])=[O:25])=[CH:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 23631094Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate

Product 1

HCID 589628521-(2-Tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acidYield 64%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Ethyl 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylate (510 mg, 0.99 mmol) was suspended in EtOH (120 mL), to which was added 1 M K2CO3 (80 mL). This mixture was stirred at R.T. for 15 h., then diluted with 1 M HCl (100 mL) and the resulting precipitate extracted into EtOAc (3×100 mL). The combined EtOAc fractions were washed with water (3×100 mL), brine (100 mL) and dried (Na2SO4). The solvent was then removed under reduced pressure to afford a crude solid which was purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant) to give 1-(2-tert-butoxy-2-oxoethyl)-4-(2-fluoro-4-iodoanilino)-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid as a white solid (64%), used directly in the next step. 1H NMR [(CD3)2SO, 400 MHz] δ 11.03 (v br s, 1H), 8.33 (s, 1H), 7.71 (dd, J=10.2, 1.9 Hz, 1H), 7.55 (dd, J=8.4, 1.0 Hz, 1H), 7.29 (t, J=8.3 Hz, 1H), 5.49 (s, 1H), 4.55 (s, 2H), 1.39 (s, 9H). HRMS (EI+) calcd C18H18FIN2O5 (M+) 488.0245, found 488.0247.

Workup

  1. extractionthe resulting precipitate extracted into EtOAc (3×100 mL)
  2. washThe combined EtOAc fractions were washed with water (3×100 mL), brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was then removed under reduced pressure
  5. customto afford a crude solid which
  6. customwas purified by column chromatography on silica gel (5% MeOH/CH2Cl2 as eluant)

Sources & evidence

ORD record
ord-8068e37d26204ba481ebc5939a495a65
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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