(S)-2,3-epoxy-2-trifluoromethylpropionic acid benzyl ester → HCID 10464546, compound

HRID 897165Notes

Reaction equation

HRID 897165 reaction equation
C([O:8][C:9](=[O:17])[C@@:10]1([C:13]([F:16])([F:15])[F:14])[O:12][CH2:11]1)C1C=CC=CC=1.[H][H]>[Pt]=O.CO>[O:12]1[CH2:11][C@@:10]1([C:13]([F:16])([F:15])[F:14])[C:9]([OH:17])=[O:8]

Participants

5

Reactant 2

HCID 10014785(S)-2,3-epoxy-2-trifluoromethylpropionic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 10464546HCID 10464546, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

Into a 500 ml three-necked round-bottomed flask equipped with a stirrer, (S)-2,3-epoxy-2-trifluoromethylpropionic acid benzyl ester (20.9 g, 84.9 mmol, 99 ee %) was charged, and 180 ml of methanol was added for dissolution. Platinum oxide (1.63 g) was added, and then, the reaction system was substituted by hydrogen. After stirring at room temperature for 4 hours, platinum oxide was filtered off. The solvent was distilled off under reduced pressure, whereupon (S)-2,3-epoxy-2-trifluoromethylpropionic acid (11.9 g) was obtained (yield: 90%).

Workup

  1. customInto a 500 ml three-necked round-bottomed flask equipped with a stirrer
  2. filtrationplatinum oxide was filtered off
  3. distillationThe solvent was distilled off under reduced pressure, whereupon (S)-2,3-epoxy-2-trifluoromethylpropionic acid (11.9 g)
  4. customwas obtained (yield: 90%)

Sources & evidence

ORD record
ord-ee5de33be4fd47aa995c76b52ed103ef
Source dataset
uspto-grants-2005_07
Patent number
US06921832B2

Reaction notes

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