1,1'-Carbonyldiimidazole → HCID 10112958, compound

HRID 2182930Notes

Reaction equation

HRID 2182930 reaction equation
[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][C:8]2[N:12]=[C:11]([C@H:13]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:14][C:15](O)=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:42][OH:43]>O1CCCC1>[NH3:9].[Cl:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][C:8]2[N:12]=[C:11]([C@H:13]([CH2:18][CH2:19][CH2:20][CH:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[CH2:14][C:15]([NH:42][OH:43])=[O:16])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 59909816HCID 59909816, compound

Product 2

HCID 222AmmoniaHCID 10112958HCID 10112958, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R)-3-{3-[(4-chlorophenoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoic acid (Preparation 57) (180 mg, 0.44 mmol) in anhydrous tetrahydrofuran (10 ml) was treated with 1,1′-carbonyldiimidazole (71 mg, 0.44 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (30 mg, 0.44 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 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 glass (53 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 brine
  6. dry with materialdried 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-7937638396fb40d0b83de8e84d81814f
Source dataset
uspto-grants-2005_05
Patent number
US06897306B2

Reaction notes

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