HCID 59909808, compound → (3R)-6-cyclohexyl-3-(3-{[3-(dimethylamino)-1-azetidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoic acid

HRID 2183038Notes

Reaction equation

HRID 2183038 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]3[CH2:29][CH:28]([N:30]([CH3:32])[CH3:31])[CH2:27]3)=[O: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]([C:24]([N:26]3[CH2:27][CH:28]([N:30]([CH3:32])[CH3:31])[CH2:29]3)=[O:25])[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 59909808HCID 59909808, compound

Product 1

HCID 23378031(3R)-6-cyclohexyl-3-(3-{[3-(dimethylamino)-1-azetidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoic acidYield 10.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-{[3-(dimethylamino)-1-azetidinyl]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate (Preparation 75) (340 mg, 0.76 mmol) in trifluoroacetic acid (10 ml) was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue azeotroped from dichloromethane. The residue was dissolved in ethyl acetate (50 ml) and washed with saturated aqueous ammonium chloride solution (50 ml) and brine (50 ml), dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a white solid (30 mg). The combined aqueous washes were extracted with dichloromethane, containing <10% methanol, (3×150 ml). The combined organic layers were dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a white solid (180 mg), combined total mass 210 mg.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue azeotroped from dichloromethane
  3. dissolutionThe residue was dissolved in ethyl acetate (50 ml)
  4. washwashed with saturated aqueous ammonium chloride solution (50 ml) and brine (50 ml)
  5. dry with materialdried over anhydrous sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-746614b77e4049f5a907896bb197f64d
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

Loading…