Hydrochloric Acid → HCID 10959481, compound

HRID 634636Notes

Reaction equation

HRID 634636 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:28])=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[CH:12][C:11]=2[NH:20][C:21](=[O:27])[CH2:22][C:23]([O:25]C)=O)=O)[CH:7]=1.CC(C)([O-])C.[K+].Cl>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:28][C:23](=[O:25])[C:22]3[C:21](=[O:27])[NH:20][C:11]4[CH:12]=[CH:13][C:14]([C:16]([F:17])([F:19])[F:18])=[CH:15][C:10]=4[C:8]=3[C:6]=2[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 86756351HCID 86756351, compound

Product 1

HCID 10959481HCID 10959481, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 3-[[2-[(5-chloro-2-hydroxyphenyl)carbonyl]-4-(trifluoromethyl)phenyl]amino]-3-oxopropanoic acid, methyl ester prepared in Step B was dissolved in THF (15 mL) and potassium t-butoxide solution (1M in THF, 1.74 mmol, 1.74 mL) was added. The reaction mixture was heated under reflux for 15 minutes. It was then acidified with 1N HCl and the organic layer was separated. The organic layer was washed with water, brine and dried (MgSO4). Evaporation of the solvent gave a yellow solid which was triturated with ethyl acetate/hexanes to afford the title compound as a yellow solid (0.48 g, 83%): mp>250° C. MS m/e 366 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 15 minutes
  3. customthe organic layer was separated
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent
  7. customgave a yellow solid which
  8. customwas triturated with ethyl acetate/hexanes

Sources & evidence

ORD record
ord-5d4e1cc32a0d473ebf27ff22843cf0c7
Source dataset
uspto-grants-2001_02
Patent number
US06184231B2

Reaction notes

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