Trifluoroacetic acid → (3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoic acid

HRID 1279817Notes

Reaction equation

HRID 1279817 reaction equation
[NH2:1][C:2]([C:4]1[N:8]=[C:7]([C@H:9]([CH2:18][CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:10][C:11]([O:13]C(C)(C)C)=[O:12])[O:6][N:5]=1)=[O:3].FC(F)(F)C(O)=O>ClCCl>[NH2:1][C:2]([C:4]1[N:8]=[C:7]([C@H:9]([CH2:18][CH2:19][CH2:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:10][C:11]([OH:13])=[O:12])[O:6][N:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86583702tert-Butyl (3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl)-6-phenylhexanoate

Product 1

HCID 11426858(3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl (3R)-3-[3-(aminocarbonyl)-1,2,4-oxadiazol-5-yl]-6-phenylhexanoate (Preparation 5) (250 mg, 0.68 mmol) in dichloromethane (10 ml) was cooled to 0° C. and treated with trifluoroacetic acid (5 ml). The mixture was stirred for 2 hours, being allowed to warm to room temperature over this time. The solvent was removed under reduced pressure and the residue was azeotroped with toluene (×2) then hexane to afford the title compound as a white solid (204 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was azeotroped with toluene (×2)

Sources & evidence

ORD record
ord-16924f3ea07d4268ba223675cc8ea667
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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