Trifluoroacetic acid → 2-{2-[1-Ethyl-3-(4-trifluoromethoxyphenyl)ureido]indan-5-ylsulfanyl}-2-methylpropionic acid

HRID 898878Notes

Reaction equation

HRID 898878 reaction equation
C([O:5][C:6](=[O:37])[C:7]([S:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[CH2:16][CH:15]([N:20]([CH2:35][CH3:36])[C:21]([NH:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1)=[O:22])[CH2:14]2)([CH3:9])[CH3:8])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:35]([N:20]([CH:15]1[CH2:14][C:13]2[C:17](=[CH:18][CH:19]=[C:11]([S:10][C:7]([CH3:8])([CH3:9])[C:6]([OH:37])=[O:5])[CH:12]=2)[CH2:16]1)[C:21]([NH:23][C:24]1[CH:25]=[CH:26][C:27]([O:30][C:31]([F:34])([F:32])[F:33])=[CH:28][CH:29]=1)=[O:22])[CH3:36]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68812777HCID 68812777, compound

Product 1

HCID 98480832-{2-[1-Ethyl-3-(4-trifluoromethoxyphenyl)ureido]indan-5-ylsulfanyl}-2-methylpropionic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-{2-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]indan-5-ylsulfanyl}-2-methylpropionic acid tert butyl ester (4.8 g; 8.91 mmol) dissolved in CH2Cl2 (15 mL) is added TFA (15 mL) and the reaction was stirred at RT for 2 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (SiO2) eluting with a hexanes-EtOAc gradient to afford 3.13 g (73%) of 2-{2-[1-ethyl-3-(4-trifluoromethoxyphenyl)ureido]indan-5-ylsulfanyl}-2-methylpropionic acid as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by flash chromatography (SiO2)
  3. washeluting with a hexanes-EtOAc gradient

Sources & evidence

ORD record
ord-28f6422eff944a709ac865085bd382a9
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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