Trifluoroacetic acid → HCID 17984479, compound

HRID 1181121Notes

Reaction equation

HRID 1181121 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][C:10]=1[CH2:30][O:31][CH3:32])(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:32][O:31][CH2:30][C:10]1[CH:11]=[C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[CH:13]=[CH:14][C:9]=1[CH2:8][CH2:7][C:6]([OH:33])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58979302HCID 58979302, compound

Product 1

HCID 17984479HCID 17984479, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 15 mL round bottomed flask was charged 3-{2-methoxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenyl}propionic acid tert-butyl ester (0.060 g, 0.13 mmol), CH2Cl2 (1.2 mL), and then trifluoroacetic acid (0.6 mL). The solution was stirred at ambient temperature under a nitrogen atmosphere for 16 h and was concentrated. The residue was diluted with CH2Cl2 (30 mL) and washed with brine. The organic layer was dried (Na2SO4), filtered, and concentrated to give a white solid (0.046 g, 89%). MS (ES) m/e 648 (M+1).

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with CH2Cl2 (30 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a01b9ad06c5e4940897738eaa8123bf7
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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