1,1'-Carbonyldiimidazole → HCID 10156141, compound

HRID 2182931Notes

Reaction equation

HRID 2182931 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([CH2:14][CH2:15][CH2:16][C@@H:17]([C:22]2[O:26][N:25]=[C:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[N:23]=2)[CH2:18][C:19](O)=[O:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:47][OH:48]>O1CCCC1>[NH3:23].[CH:8]1([CH2:14][CH2:15][CH2:16][C@@H:17]([C:22]2[O:26][N:25]=[C:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=3)[N:23]=2)[CH2:18][C:19]([NH:47][OH:48])=[O:20])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 69778090HCID 69778090, compound

Product 2

HCID 222AmmoniaHCID 10156141HCID 10156141, compoundYield 143.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R)-6-cyclohexyl-3-[3-(2-pyridinylmethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid trifluoroacetate (Preparation 59) (214 mg, 0.45 mmol) in anhydrous tetrahydrofuran (5 ml) was treated with 1,1′-carbonyldiimidazole (194 mg, 1.20 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (83 mg, 1.20 mmol) was then added and the mixture stirred for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The layers were separated and the organic phase was washed with water then brine, dried over anhydrous magnesium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.88 ammonia (95:5:0.5) to afford the title compound as a colourless oil (120 mg).

Workup

  1. stirringthe mixture stirred for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe organic phase was washed with water
  6. dry with materialbrine, dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customthe solvent removed under reduced pressure
  9. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-a9540fcfe22443c89734ff2d20111533
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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