2-((1R)-1-{2-[(Benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N,N-dimethyl-1,3-oxazole-4-carboxamide → (R)-2-(6-cyclohexyl-1-(hydroxyamino)-1-oxohexan-3-yl)-N,N-dimethyloxazole-4-carboxamide

HRID 1279785Notes

Reaction equation

HRID 1279785 reaction equation
C([O:8][NH:9][C:10](=[O:32])[CH2:11][C@H:12]([C:22]1[O:23][CH:24]=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[N:26]=1)[CH2:13][CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)C1C=CC=CC=1.[H][H]>C(O)C.[Pd]>[CH:16]1([CH2:15][CH2:14][CH2:13][C@@H:12]([C:22]2[O:23][CH:24]=[C:25]([C:27]([N:29]([CH3:31])[CH3:30])=[O:28])[N:26]=2)[CH2:11][C:10]([NH:9][OH:8])=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 599097552-((1R)-1-{2-[(Benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N,N-dimethyl-1,3-oxazole-4-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 10132648(R)-2-(6-cyclohexyl-1-(hydroxyamino)-1-oxohexan-3-yl)-N,N-dimethyloxazole-4-carboxamideYield 92.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-((1R)-1 -{2-[(benzyloxy)amino]-2-oxoethyl}-4-cyclohexylbutyl)-N,N-dimethyl-1,3-oxazole-4-carboxamide (Preparation 66) (100 mg, 0.23 mmol) in ethanol (5 ml) was treated with 5% palladium on barium sulphate (50 mg), pressurised to 1 atm with hydrogen in a sealed vessel and the mixture was stirred at room temperature for 2 hours. The solution was filtered through Arbocel® and the solvent removed from the filtrate under reduced pressure. The residue was azeotroped from dichloromethane (×3) then dichloromethane:ether (1 ml:4 ml) to afford the title compound as a foam (75 mg).

Workup

  1. filtrationThe solution was filtered through Arbocel®
  2. customthe solvent removed from the filtrate under reduced pressure
  3. customThe residue was azeotroped from dichloromethane (×3)

Sources & evidence

ORD record
ord-bc6ab79feec44713bb25d2797375610f
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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