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

HRID 1830188Notes

Reaction equation

HRID 1830188 reaction equation
[OH:1][CH:2]([C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1)[CH:3]([NH:6][C:7](=[O:28])[CH:8]([CH2:17][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](=[O:16])[N:11]1[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+]>>[O:16]=[C:10]([N:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:9][CH:8]([CH2:17][S:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:20])=[O:19])[C:7]([NH:6][CH:3]([C:2]([C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1)=[O:1])[CH2:4][CH3:5])=[O:28]

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22054105N-{1-[Hydroxy-(5-pyridin-4-yl-[1,3,4]oxadiazol-2-yl)-methyl]-propyl}-4-oxo-2-benzylsulfonylmethyl-4-pyrrolidin-1-yl-butyramideHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 101662494-Oxo-2-benzylsulfonylmethyl-n-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-pyrrolidin-1-yl-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 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 102 mg of 4-Oxo-2-benzylsulfonylmethyl-N-[1-(5-pyridin-4-yl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-4-pyrrolidin-1-yl-butyramide; H1NMR (DMSO-d): 9.0–8.85(3H, m), 8.1–8(2H, m), 7.44–7.3(5H, m), 5.05–4.9(1H, m), 4.55–4.35(2H, m), 3.4–3.(8H, m), 2.6–2.4(1H, m), 2.05–1.9(1H, m), 1.9–1.6(5H, m), 0.96(3H, t); MS: 552.6(M−1), 554.6(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-244ca0144d94468bb1d5ad86cf8f3c52
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

Loading…