1,1'-Carbonyldiimidazole → (3R)-6-Cyclohexyl-N-hydroxy-3-{3-[(phenylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl}hexanamide

HRID 1279783Notes

Reaction equation

HRID 1279783 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][S:21]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)(=[O:23])=[O:22])[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.[NH2:43][OH:44]>O1CCCC1>[NH3:16].[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:15]2[O:19][N:18]=[C:17]([CH2:20][S:21]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)(=[O:23])=[O:22])[N:16]=2)[CH2:11][C:12]([NH:43][OH:44])=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 59909787HCID 59909787, compound

Product 2

HCID 222AmmoniaHCID 10274651(3R)-6-Cyclohexyl-N-hydroxy-3-{3-[(phenylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl}hexanamideYield 49.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R)-6-cyclohexyl-3-{3-[(phenylsulfonyl)methyl]-1,2,4-oxadiazol-5-yl)hexanoic acid (Preparation 55) (60 mg, 0.14 mmol) in anhydrous tetrahydrofuran (4 ml) was treated with 1,1′-carbonyldiimidazole (25 mg, 0.15 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (10 mg, 0.14 mmol) was then added and the mixture was stirred for 18 hours. The solvent was removed under reduced pressure and 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 an oil (15 mg).

Workup

  1. stirringthe mixture was stirred for 18 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-060991310e4c44e797a249c5eedda6fd
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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