Trifluoroacetic acid → HCID 59909829, compound

HRID 1279833Notes

Reaction equation

HRID 1279833 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:37]=[CH:36][N:35]=[CH:34][CH:33]=4)[CH2:28][CH2:27]3)=[O:25])[N:20]=2)[CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]4[CH:33]=[CH:34][N:35]=[CH:36][CH:37]=4)[CH2:28][CH2:27]3)=[O:25])[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909821HCID 59909821, compound

Product 1

HCID 59909829HCID 59909829, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-{[4-(4-pyridinyl)-1-piperidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate (Preparation 31) (376 mg, 0.74 mmol) in dichloromethane (15 ml) was cooled to 0° C. and treated with trifluoroacetic acid (5 ml). The resulting mixture was stirred for 3 hours being allowed to warm to room temperature over this time. The solvent was removed under reduced pressure and the residue azeotroped from toluene (×3) then dichloromethane. A saturated solution of sodium carbonate was added to the residue until a pH of 12 was achieved followed by dropwise addition of an aqueous citric acid solution solution (10% w/v) until the pH became 3.5. The solution was then diluted with water and extracted with ethyl acetate (×3). The combined organic layers were washed with brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a white solid (310 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene (×3)
  3. additionA saturated solution of sodium carbonate was added to the residue until a pH of 12
  4. additionwas achieved followed by dropwise addition of an aqueous citric acid solution solution (10% w/v) until the pH
  5. additionThe solution was then diluted with water
  6. extractionextracted with ethyl acetate (×3)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulphate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-5124dd70e476421aa71f27e8cb95306b
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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