Trifluoroacetic acid → HCID 59759049, compound

HRID 914519Notes

Reaction equation

HRID 914519 reaction equation
C([O:5][C:6](=[O:34])[C:7]([CH3:33])([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=3)=[CH:20][CH:19]=2)[N:14]=1)[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH3:33][C:7]([S:9][C:10]1[S:11][CH:12]=[C:13]([CH2:15][CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[CH:20][CH:19]=2)[N:14]=1)([CH3:8])[C:6]([OH:34])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59759128HCID 59759128, compound

Product 1

HCID 59759049HCID 59759049, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-2-[(4-{2-[(4′-nitrobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]propionic acid tert-butyl ester (3.3 g) synthesized in Example 733-1 in dichloromethane (10 mL) was added trifluoroacetic acid (30 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated, poured into water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure. Thereto was added diisopropyl ether, and the resulting crystals were collected by filtration to give the title compound (2.4 g) as yellow crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure
  7. additionThereto was added diisopropyl ether
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-03afff37e2084e4fa5d45f4d975b32b7
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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