Chloroacetic Acid → HCID 10740435, compound

HRID 1736228Notes

Reaction equation

HRID 1736228 reaction equation
[Cl:1][CH2:2][C:3]([OH:5])=[O:4].[F:6][C:7]1[C:8]([CH2:40]O)=[C:9]([F:39])[C:10]2[O:15][C:14]([C:16]3[CH:21]=[CH:20][C:19]([NH:22]C(=O)C(C)(C)C)=[C:18]([F:29])[CH:17]=3)=[CH:13][C:12](=[O:30])[C:11]=2[C:31]=1[NH:32]C(=O)C(C)(C)C>S(=O)(=O)(O)O>[NH2:32][C:31]1[C:11]2[C:12](=[O:30])[CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([NH2:22])=[C:18]([F:29])[CH:17]=3)[O:15][C:10]=2[C:9]([F:39])=[C:8]([CH2:40][O:4][C:3](=[O:5])[CH2:2][Cl:1])[C:7]=1[F:6]

Participants

4

Reactant 2

HCID 300Chloroacetic AcidHCID 10673123HCID 10673123, compound

Product 1

HCID 10740435HCID 10740435, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
100 °C

Procedure

100 g (1.06 mol) of chloroacetic acid and 30 mL of sulfuric acid were added to 10.8 g (20.0 mmol) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-7-hydroxymethyl-5-pivaloylamino-4H-1-benzopyran-4-one obtained in EXAMPLE 118 (4), and the mixture was stirred at 100° C. for 20 minutes. The reaction solution was poured into 1 L of ice-water and the mixture was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was triturated with diisopropyl ether, to give 8.00 g of Compound 159 (yield: 97%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-39484111e256428781e46e7335e14a45
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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