Trifluoroacetic acid → 2-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid

HRID 914388Notes

Reaction equation

HRID 914388 reaction equation
C([O:5][C:6](=[O:34])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][C:17]([O:19][CH2:20][CH:21]2[C:33]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[N:15]=1)([CH3:9])[CH3:8])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:23]1[C:22]2[CH:21]([CH2:20][O:19][C:17](=[O:18])[CH2:16][C:14]3[N:15]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:34])=[O:5])[S:12][CH:13]=3)[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]=2[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597593352-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester

Product 1

HCID 597588412-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acidYield 108.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-({4-[2-(9H-fluorene-9-ylmethoxy)-2-oxoethyl]-1,3-thiazol-2-yl}thio)-2-methylpropionic acid tert-butyl ester (260 g) obtained in Example 461-1 in dichloromethane (400 mL) was added trifluoroacetic acid (100 mL), and the mixture was stirred at room temperature overnight and heated at 45° C. with stirring for 8 hr. The reaction mixture was concentrated, ethyl acetate was added, and the organic layer was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1) to give the title compound (250 g) as a yellow oil.

Workup

  1. temperatureheated at 45° C.
  2. stirringwith stirring for 8 hr
  3. concentrationThe reaction mixture was concentrated
  4. additionethyl acetate was added
  5. washthe organic layer was washed with saturated brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe obtained residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-58ddd6cbb2534a9192635441fc59a2c3
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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