Trifluoroacetic acid → (3R)-3-(3-{[Benzyl(methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoic Acid

HRID 1279835Notes

Reaction equation

HRID 1279835 reaction equation
[CH2:1]([N:8]([CH3:34])[C:9]([C:11]1[N:15]=[C:14]([C@H:16]([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:17][C:18]([O:20]C(C)(C)C)=[O:19])[O:13][N:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:8]([CH3:34])[C:9]([C:11]1[N:15]=[C:14]([C@H:16]([CH2:25][CH2:26][CH2:27][CH:28]2[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:17][C:18]([OH:20])=[O:19])[O:13][N:12]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59909818HCID 59909818, compound

Product 1

HCID 59909839(3R)-3-(3-{[Benzyl(methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoic AcidYield 86.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-3-(3-{[benzyl(methyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)-6-cyclohexylhexanoate (Preparation 33) (296 mg, 0.63 mmol) in dichloromethane (4 ml) was treated with trifluoroacetic acid (1 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 17 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene to afford the title compound (226 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene

Sources & evidence

ORD record
ord-27a5be5a53d54b468e9a81bf1ac45108
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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