Trifluoroacetic acid → (3R)-6-cyclohexyl-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanoic acid

HRID 1279847Notes

Reaction equation

[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH:24]([CH3:26])[CH3:25])[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>>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH:24]([CH3:26])[CH3:25])[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 59909769HCID 59909769, compound

Product 1

HCID 59909812(3R)-6-cyclohexyl-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanoic acidYield 103.4%

Procedure

tert-Butyl (3R)-6-cyclohexyl-3-(3-isopropyl-1,2,4-oxadiazol-5-yl)hexanoate (Preparation 46) (250 mg, 0.69 mmol) was treated with trifluoroacetic acid (5 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 45 minutes. The solvent was removed under reduced pressure and the residue azeotroped from toluene then dichloromethane to afford the title compound as a white solid (220 mg).

Workup

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

Sources & evidence

ORD record: ord-da6a350b559646cfb9658410b72b3865
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448278B2

Reaction notes

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