Triacetoxyperiodinane → HCID 10281411, compound

HRID 1830182Notes

Reaction equation

HRID 1830182 reaction equation
[OH:1][CH:2]([C:30]1[O:31][C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[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]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)=[O:11])[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+]>>[N:12]1([C:10](=[O:11])[CH2:9][CH:8]([CH2:18][S:19]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)(=[O:20])=[O:21])[C:7]([NH:6][CH:3]([C:2]([C:30]2[O:31][C:32]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[N:33][N:34]=2)=[O:1])[CH2:4][CH3:5])=[O:29])[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22054100HCID 22054100, compoundHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 10281411HCID 10281411, compound

Procedure

This amide was treated with Dess-Martin periodinane (371 mg, 0.75 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 224 mg of 4-morpholin-4-yl-4-oxo-2-benzylsulfonylmethyl-N-[1-(5-phenyl-[1,3,4]oxadiazole-2-carbonyl)-propyl]-butyramide; H1 NMR(DMSO-d): 8.9, 8.84 (1H, d, d, NH, diastereomeric), 8.1–8(2H, m), 7.7–7.6(3H, m), 7.4–7.3(5H, m),5.1–4.9(1H, m), 4.5–4.3(2H, m), 3.6–3.3(11H, m), 3.12–3(1H, m), 2.65–2.5(1H, m), 2–1.9(1H, m), 1.8–1.7(1H, m), 0.96(3H, t); MS: 567.6(M−1), 569.4(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-dc3d0291aa5840d1870e8d9fedd138af
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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