Triethylamine → HCID 59432150, compound

HRID 506489Notes

Reaction equation

HRID 506489 reaction equation
[NH2:1][CH:2]([CH:8]([OH:13])[C:9]([F:12])([F:11])[F:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[F:14][C:15]1[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[C:17]([C:24]([F:27])([F:26])[F:25])[CH:16]=1.C(N(CC)CC)C>C1COCC1>[F:12][C:9]([F:10])([F:11])[CH:8]([OH:13])[CH:2]([NH:1][C:19](=[O:20])[C:18]1[CH:22]=[CH:23][C:15]([F:14])=[CH:16][C:17]=1[C:24]([F:27])([F:25])[F:26])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6882554-Fluoro-2-(trifluoromethyl)benzoic acidHCID 15634552HCID 15634552, compound

Product 1

HCID 59432150HCID 59432150, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.7 g (8.5 mmol) of ethyl 2-amino-4,4,4-trifluoro-3-hydroxybutyrate were dissolved in THF, and initially 1.8 g of 4-fluoro-2-trifluoromethylbenzoic acid and 2.6 g (25.4 mmol) of triethylamine and then, at 5° C., 1.9 g (8.5 mmol) of bis(2-oxo-3-oxazolinidylphosphoryl chloride were added. The mixture was stirred at RT for 16 h. The reaction solution was then concentrated, and the residue was diluted with water and extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. This gave 3.1 g (93% of theory) of the title compound as a colorless residue.

Workup

  1. concentrationThe reaction solution was then concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with ethyl acetate
  4. customThe combined organic phases were dried
  5. customthe solvent was removed

Sources & evidence

ORD record
ord-a1eb04bf736d47c4a21d42c4c66297f6
Source dataset
uspto-grants-2010_08
Patent number
US07786046B2

Reaction notes

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