Trifluoroacetic acid → HCID 23378032, compound

HRID 2183005Notes

Reaction equation

HRID 2183005 reaction equation
C([O:5][C:6](=[O:33])[CH2:7][C@H:8]([C:18]1[O:22][N:21]=[C:20]([C:23]([N:25]2[CH2:28][CH:27]([C:29]([O:31][CH3:32])=[O:30])[CH2:26]2)=[O:24])[N:19]=1)[CH2:9][CH2:10][CH2:11][CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:12]1([CH2:11][CH2:10][CH2:9][C@@H:8]([C:18]2[O:22][N:21]=[C:20]([C:23]([N:25]3[CH2:26][CH:27]([C:29]([O:31][CH3:32])=[O:30])[CH2:28]3)=[O:24])[N:19]=2)[CH2:7][C:6]([OH:33])=[O:5])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69778246HCID 69778246, compound

Product 1

HCID 23378032HCID 23378032, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 1-[(5-{(1R)-1-[2-(tert-butoxy)-2-oxoethyl]-4-cyclohexylbutyl}-1,2,4-oxadiazol-3-yl)carbonyl]-3-azetidinecarboxylate (Preparation 42) (225 mg, 0.48 mmol) in dichloromethane (8 ml) was treated with trifluoroacetic acid (4 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 5 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene (×2). The residue was dissolved in ethyl acetate and washed sequentially with a saturated aqueous solution of sodium citrate and brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as an oil (200 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene (×2)
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed sequentially with a saturated aqueous solution of sodium citrate and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9887b86aec514fddb8ea4d2731b25e41
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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