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

HRID 1279885Notes

Reaction equation

HRID 1279885 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.C([Li])CCC.[CH:18]1([CH2:24][CH2:25][CH2:26][C@@H:27]([C:36]2[O:40][N:39]=[C:38]([CH2:41]OS(C3C=CC(C)=CC=3)(=O)=O)[N:37]=2)[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>O1CCCC1>[CH:18]1([CH2:24][CH2:25][CH2:26][C@@H:27]([C:36]2[O:40][N:39]=[C:38]([CH2:41][C:2]3[NH:1][CH:5]=[CH:4][N:3]=3)[N:37]=2)[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:33])[CH3:34])=[O:30])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 521262tert-butyl 1H-imidazole-1-carboxylateHCID 16747945tert-Butyl (3R)-6-cyclohexyl-3-[3-({[(4-methylphenyl)sulfonyl]oxy}methyl)1,2,4-oxadiazol-5-yl]hexanoateHCID 178418339Butyllithium

Product 1

HCID 59909809tert-butyl (3R)-6-cyclohexyl-3-[3-(1H-imidazol-2-ylmethyl)-1,2,4-oxadiazol-5-yl]hexanoateYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 1H-imidazole-1-carboxylate (133 mg, 0.79 mmol) in anhydrous tetrahydrofuran (2 ml), cooled to −78° C., treated with n-butyl lithium, 2.5M in hexanes (320 μl, 0.79 mmol) and stirred under a nitrogen atmosphere for 1 hour. A solution of tert-butyl (3R)-6-cyclohexyl-3-[3-(([(4-methylphenyl)sulfonyl]oxy)methyl)-1,2,4-oxadiazol-5- yl]hexanoate (Preparation 92) (400 mg, 0.79 mmol) in anhydrous tetrahydrofuran (2 ml) was added slowly and the mixture was allowed to warm to room temperature and stirred at this temperature for 18 to hours. The reaction mixture was partitioned between ethyl acetate (30 ml) and water (30 ml). The organic layer was washed once more with water (20 ml), dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure to afford the title compound as a pale yellow oil (307 mg).

Workup

  1. stirringstirred at this temperature for 18 to hours
  2. customThe reaction mixture was partitioned between ethyl acetate (30 ml) and water (30 ml)
  3. washThe organic layer was washed once more with water (20 ml)
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-c8c5cc5a8dd548599d150bce3899ef7d
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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