Water → HCID 10464546, compound

HRID 897167Notes

Reaction equation

HRID 897167 reaction equation
C1([O:7][C:8](=[O:16])[C@@:9]2([C:12]([F:15])([F:14])[F:13])[O:11][CH2:10]2)C=CC=CC=1.O.[OH-].[Na+]>CO>[O:11]1[CH2:10][C@@:9]1([C:12]([F:15])([F:14])[F:13])[C:8]([OH:16])=[O:7]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593755(S)-2,3-epoxy-2-trifluoromethylpropionic acid phenyl ester

Product 1

HCID 10464546HCID 10464546, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Into a 100 ml three-necked round-bottomed flask equipped with a dropping funnel and a stirrer, the (S)-2,3-epoxy-2-trifluoromethylpropionic acid phenyl ester (7.2 g, 31.0 mmol) obtained in Example 7, methanol (20 ml) and water (20 ml) were charged and cooled to 0° C. on an ice bath, whereupon 3N sodium hydroxide aqueous solution (30 ml, 90 mmol) was dropwise added over a period of one hour by means of the dropping funnel, and stirring was further carried out at the same temperature for one hour. After completion of the reaction, methanol was distilled off, followed by extraction with diisopropyl ether (30 ml×twice). Then, hydrochloric acid was added to adjust the pH to 3, followed by extraction with ethyl acetate (30 ml×3 times). The obtained organic layer was dried over anhydrous magnesium sulfate, followed by filtration and concentration to obtain the desired (S)-2,3-epoxy-2-trifluoromethylpropionic acid (4.17 g, 26.7 mmol, yield: 87%, optical purity: 78% ee).

Workup

  1. customInto a 100 ml three-necked round-bottomed flask equipped with a dropping funnel and a stirrer
  2. additionwas dropwise added over a period of one hour by means of the dropping funnel
  3. distillationwas distilled off
  4. extractionfollowed by extraction with diisopropyl ether (30 ml×twice)
  5. additionThen, hydrochloric acid was added
  6. extractionfollowed by extraction with ethyl acetate (30 ml×3 times)
  7. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfollowed by filtration and concentration

Sources & evidence

ORD record
ord-c4055b7924f244f1b642a4723df5f7d4
Source dataset
uspto-grants-2005_07
Patent number
US06921832B2

Reaction notes

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