Acetic Acid → HCID 58477352, compound

HRID 876543Notes

Reaction equation

HRID 876543 reaction equation
O[C:2]1[C:10]([C:11](=[O:25])[CH2:12][C:13](=[O:24])[C:14]2[C:15]([C:20]([F:23])([F:22])[F:21])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([O-:6])=[O:5].Cl.[C:27](O)(=O)C>>[O:25]=[C:11]1[C:10]2[C:2](=[C:3]([C:4]([O:6][CH3:27])=[O:5])[CH:7]=[CH:8][CH:9]=2)[O:24][C:13]([C:14]2[C:15]([C:20]([F:23])([F:21])[F:22])=[N:16][CH:17]=[CH:18][CH:19]=2)=[CH:12]1

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 178520869HCID 178520869, compound

Product 1

HCID 58477352HCID 58477352, compoundYield 23%

Procedure

A mixture of 2-hydroxy-3-(3-oxo-3-(2-(trifluoromethyl)pyridin-3-yl)propanoyl)benzoate 39 (600 mg, 1.46 mmol) and con. HCl (1 mL) in acetic acid (5 mL) was heated at 100° C. for 4 hours. The reaction mixture was concentrated and sat. aq NaHCO3 was added. The mixture was extracted with ethyl acetate and the combined organics were washed with brine, dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography to give 40 (120 mg, 23% yield).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsat. aq NaHCO3 was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-7a29e0bfee2d49f683290a527ceba01f
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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