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

HRID 1279780Notes

Reaction equation

HRID 1279780 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][O:21][CH3:22])[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.[NH2:36][OH:37]>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][O:21][CH3:22])[N:16]=2)[CH2:11][C:12]([NH:36][OH:37])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 443297Hydroxyamine hydrochlorideHCID 59909760(3R)-6-cyclohexyl-3-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid

Product 2

HCID 222AmmoniaHCID 9880364(3R)-6-cyclohexyl-N-hydroxy-3-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]hexanamideYield 56.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (3R)-6-cyclohexyl-3-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]hexanoic acid (Preparation 49) (250 mg, 0.81 mmol) in anhydrous tetrahydrofuran (10 ml) was treated with 1,1′-carbonyldiimidazole (130 mg, 0.81 mmol) and the mixture stirred at room temperature under a nitrogen atmosphere for 2 hours. Hydroxylamine hydrochloride (56 mg, 0.81 mmol) was then added and the mixture 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 (75 mg).

Workup

  1. stirringthe mixture 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-ded263697d5a47a7a9d76d64eb7d4df1
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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