Triacetoxyperiodinane → (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-trifluoromethyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide

HRID 1796162Notes

Reaction equation

HRID 1796162 reaction equation
[CH:1]1([CH2:7][C@H:8]([CH2:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[C:9]([NH:11][C@H:12]([CH:15]([OH:25])[C:16]2[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=2)[CH2:13][CH3:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH:1]1([CH2:7][C@H:8]([CH2:26][C:27]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[O:28])[C:9]([NH:11][C@H:12]([C:15]([C:16]2[N:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[O:18][N:17]=2)=[O:25])[CH2:13][CH3:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 69619419(R)-2-Cyclohexylmethyl-N-{(S)-1-[hydroxy-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-butyramide

Product 1

HCID 58619503(R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-trifluoromethyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-2-Cyclohexylmethyl-N-{(S)-1-[hydroxy-(5-trifluoromethyl-1,2,4-oxadiazol-3-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-butyramide (324 mg, 0.661 mmol) in methylene chloride (10 ml) was treated with Dess Martin periodinane (308 mg, 0.726 mmol) and stirred at room temperature for 90 minutes. The reaction mixture was washed with an aqueous solution of Na2S2O3 (0.26M), saturated aqueous bicarbonate solution and water, dried over Na2SO4 and the solvent evaporated under reduced pressure. The crude was purified by flash chromatography eluting with a mixture of ethyl acetate and heptane to give (R)-2-Cyclohexylmethyl-4-morpholin-4-yl-4-oxo-N-[(S)-1-(5-trifluoromethyl-1,2,4-oxadiazole-3-carbonyl)-propyl]-butyramide as an off white solid (10 mg).

Workup

  1. washThe reaction mixture was washed with an aqueous solution of Na2S2O3 (0.26M), saturated aqueous bicarbonate solution and water
  2. dry with materialdried over Na2SO4
  3. customthe solvent evaporated under reduced pressure
  4. customThe crude was purified by flash chromatography
  5. washeluting with a mixture of ethyl acetate and heptane

Sources & evidence

ORD record
ord-cfa883f21b8b4ae8838fcc8be8eea767
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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