1,1'-Carbonyldiimidazole → (3R)-6-cyclohexyl-N-hydroxy-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanamide

HRID 1279778

Reaction equation

HRID 1279778 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH3:20])[N:16]=2)[CH2:11][C:12](O)=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:34][OH:35]>O1CCCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH3:20])[N:16]=2)[CH2:11][C:12]([NH:34][OH:35])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 59909792(3R)-6-cyclohexyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanoic acid

Product 1

HCID 9944011(3R)-6-cyclohexyl-N-hydroxy-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanamideYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R)-6-cyclohexyl-3-(3-methyl-1,2,4-oxadiazol-5-yl)hexanoic acid (Preparation 45) (170 mg, 0.61 mmol) in anhydrous tetrahydrofuran (2 ml) was treated with 1,1′-carbonyldiimidazole (98 mg, 0.61 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 20 minutes. Hydroxylamine hydrochloride (42 mg, 0.61 mmol) was then added and the mixture stirred for 18 hours. The solvent was removed under reduced pressure and the residue partitioned between hydrochloric acid (0.5M) and ethyl acetate. The layers were separated and the organic phase was washed with water, dried over anhydrous sodium sulphate, filtered and solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2) to afford the title compound as an oil (82 mg).

Workup

  1. stirringthe mixture stirred for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between hydrochloric acid (0.5M) and ethyl acetate
  4. customThe layers were separated
  5. washthe organic phase was washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. filtrationfiltered
  8. customsolvent removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (98:2)

Sources & evidence

ORD record
ord-008c1769b51748e3801a78a8f82af7c9
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Linked notes

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