Ethyl chloroformate → HCID 22268766, compound

HRID 270234Notes

Reaction equation

HRID 270234 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[C:9]([O:11]C)=[O:10])=O.C([O-])([O-])=O.[K+].[K+].[CH2:28]([O:30][C:31](Cl)=[O:32])[CH3:29]>C1COCC1>[CH2:28]([O:30][C:31]([NH:5][C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([C:16]([F:17])([F:18])[F:19])[CH:15]=1)[C:9]([OH:11])=[O:10])=[O:32])[CH3:29]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 22268778HCID 22268778, compound

Product 1

HCID 22268766HCID 22268766, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-amino-5-(trifluoromethyl)benzoate (cf. procedures (116a) and (80a); 236 mg, 1.01 mmol) was dissolved in THF (11 mL) and the resulting solution was charged successively with K2CO3 (1.6 mL of a 2.0 M aq. solution) and ethylchloroformate (258 mg, 2.7 mmol). The reaction was stirred at RT for 48 h, concentrated in vacuo, and diluted with EtOAc. The organic phase was washed with sat. NaHCO3, water (2×), and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. This product was dissolved in 3:1 THF/MeOH (8 mL) and the resultant solution was charged with lithium hydroxide (2 mL of a 1N solution). The reaction was stirred for 14 h, acidified with 1N HCl, and extracted with EtOAc (2×). The organic extracts were combined, washed with water, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo to provide 3-(ethoxycarbonyl)amino-5-(trifluoromethyl)benzoic acid. MS found: (M−H)−=276.1.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc
  3. washThe organic phase was washed with sat. NaHCO3, water (2×), and brine
  4. dry with materialbefore being dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThis product was dissolved in 3:1 THF/MeOH (8 mL)
  8. additionthe resultant solution was charged with lithium hydroxide (2 mL of a 1N solution)
  9. stirringThe reaction was stirred for 14 h
  10. extractionextracted with EtOAc (2×)
  11. washwashed with water
  12. washwashed with brine
  13. dry with materialdried (Na2SO4)
  14. filtrationfiltered
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf1458947dcd4222a4cd462af5b0f8c0
Source dataset
uspto-grants-2008_11
Patent number
US07449493B2

Reaction notes

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