tert-butyl (3R)-6-cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoate → (3R)-6-cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid

HRID 1279886Notes

Reaction equation

HRID 1279886 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][C:25]3[NH:26][CH:27]=[CH:28][N:29]=3)[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]([CH2:24][C:25]3[NH:29][CH:28]=[CH:27][N:26]=3)[N:20]=2)[CH2:11][C:12]([OH:14])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 59909809tert-butyl (3R)-6-cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoate

Product 1

HCID 59909753(3R)-6-cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acidYield 133.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-butyl (3R)-6cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoate (Preparation 102) (530 mg, 1.32 mmol) was treated with trifluoroacetic acid (10 ml) and stirred at room temperature for 1.5 hours. The solvent was removed under reduced pressure and the residue azeotroped from toluene (3×30 ml) and dichloromethane (2×30 ml) to afford the title compound (609 mg).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from toluene (3×30 ml) and dichloromethane (2×30 ml)

Sources & evidence

ORD record
ord-19d6acc39c6d4bfe975cdf268d3f169c
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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