Triacetoxyperiodinane → N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramide

HRID 1830178Notes

Reaction equation

HRID 1830178 reaction equation
[OH:1][CH:2]([C:30]1[O:31][C:32]([CH2:35][O:36][CH3:37])=[N:33][N:34]=1)[CH:3]([NH:6][C:7](=[O:29])[CH:8]([CH2:18][S:19]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)(=[O:21])=[O:20])[CH2:9][C:10](=[O:17])[N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:4][CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[CH3:37][O:36][CH2:35][C:32]1[O:31][C:30]([C:2]([CH:3]([NH:6][C:7](=[O:29])[CH:8]([CH2:18][S:19]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:21])=[O:20])[CH2:9][C:10](=[O:17])[N:11]2[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]2)[CH2:4][CH3:5])=[O:1])=[N:34][N:33]=1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22054075N-{1-[hydroxy-(5-methoxymethyl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramideHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 22054117N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramide

Procedure

The amide then was treated with Dess-Martin periodinane (180 mg, 0.364 mmol) at room temperature. After stirring for 1 hour, 5 mls of saturated Na2S2O3—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 26 mgs of N-[1-(5-Methoxymethyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-oxo-2-benzylsulfonylmethyl-4-piperidin-1-yl-butyramide; H1 NMR(CDCl3): 8, 7.7(1H, d,d, NH, diastereomeric), 7.4–7.2(5H, m), 5.3–5.1(1H, m), 4.6(2H, s, OCH2), 4.3–4.1(3H, m), 3.8–3.2(9H, m), 3–2.4(2H, m), 2.2–1.4(8H, m), 0.95(3H, t); MS: 535.7(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-b2e724f5baf8466c94bf7eea91762733
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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