Trifluoroacetic acid → HCID 54431202, compound

HRID 1781631Notes

Reaction equation

HRID 1781631 reaction equation
[CH2:1]([O:3][C:4](=[O:23])[CH:5]([S:14][CH2:15][C:16]([O:18]C(C)(C)C)=[O:17])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:3][C:4](=[O:23])[CH:5]([S:14][CH2:15][C:16]([OH:18])=[O:17])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 54496316HCID 54496316, compound

Product 1

HCID 54431202HCID 54431202, compoundYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5.6 g (16.5 mmol) of 2-tert-butyloxycarbonylmethylthio-4-phenyl-butyric acid ethyl ester are placed at room temperature in 60 ml of dichloromethane. 3.8 ml (49.6 mmol) of trifluoro-acetic acid are added and the mixture is stirred for 16 hours at room temperature, then a further 3.8 ml of trifluoroacetic acid is added and the mixture is stirred for 24 hours at room temperature and then washed in succession with 25 ml of water and 25 ml of saturated sodium chloride solution. The aqueous phases are then washed with 2550 ml of dichloro-methane. The combined organic phases are dried over sodium sulfate, filtered and concentrated by evaporation. 4.86 g (100% of theory) of crude 2-carboxymethylthio-4-phenyl-butyric acid ethyl ester are obtained in the form of a brown oil.

Workup

  1. stirringthe mixture is stirred for 24 hours at room temperature
  2. washwashed in succession with 25 ml of water and 25 ml of saturated sodium chloride solution
  3. washThe aqueous phases are then washed with 2550 ml of dichloro-methane
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-ea5b8ee1ea694bff967d8ba3b4ba4b90
Source dataset
uspto-grants-1997_05
Patent number
US05633379

Reaction notes

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