Triacetoxyperiodinane → 4-Oxo-2-benzylsulfonyl-methyl-4-piperidin-1-yl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide

HRID 1830186Notes

Reaction equation

HRID 1830186 reaction equation
[OH:1][CH:2]([C:30]1[O:31][C:32]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)=[N:33][N:34]=1)[CH:3]([NH:6][C:7](=[O:29])[C:8]([CH3:28])([S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])[CH2:9][C:10]([N:12]1[CH2:17][CH2:16]O[CH2:14][CH2:13]1)=[O:11])[CH2:4][CH3:5].[CH3:41]C(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[O:11]=[C:10]([N:12]1[CH2:17][CH2:16][CH2:41][CH2:14][CH2:13]1)[CH2:9][C:8]([CH3:28])([S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:19])=[O:20])[C:7]([NH:6][CH:3]([C:2]([C:30]1[O:31][C:32]([C:35]2[CH:40]=[CH:39][N:38]=[CH:37][CH:36]=2)=[N:33][N:34]=1)=[O:1])[CH2:4][CH3:5])=[O:29]

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 18470521Sodium bicarbonate sodium sulfiteHCID 22054030N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-morpholin-4-yl-4-oxo-2-benzylsulfonyl-methyl-butyramide

Product 1

HCID 694356444-Oxo-2-benzylsulfonyl-methyl-4-piperidin-1-yl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide

Procedure

This amide was treated with Dess-Martin periodinane (222.7 mg, 0.45 mmol) at room temperature. After stirring for 1 hour, 5 mls of saturated Na2SO3—NaHCO3 were added. After a further 0.5 hours, the reaction mixture was extracted with ethyl acetate, washed with brine, dried with MgSO4 and concentrated. The residue was purified with silica gel column chromatography to yield 78 mg of 4-oxo-2-benzylsulfonyl-methyl-4-piperidin-1-yl-N-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide; H1 NMR(DMSO-d): 9.0–8.85(3H, m), 8.1–8(2H, m), 7.44–7.3(5H, m), 5–4.9(1H, m), 4.5–4.3(2H, m), 3.6–3.2(11H, m), 3.15–3.05(1H, m), 2.7–2.5(1H, m), 2.05–1.9(1H, m), 1.8–1.7(1H, m), 0.96(3H, t); MS: 568.6(M−1), 570.6(M+1).

Workup

  1. waitAfter a further 0.5 hours
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-8772fc0f8758494fb7f7cf4d252b56c6
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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