Triacetoxyperiodinane → HCID 22053959, compound

HRID 1830193Notes

Reaction equation

HRID 1830193 reaction equation
[CH:1]1([CH2:7][CH: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][CH:12]([CH:15]([OH:25])[C:16]2[O:17][C:18]3[C:19]([N:24]=2)=[N:20][CH:21]=[CH:22][CH:23]=3)[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.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[CH:1]1([CH2:7][CH:8]([CH2:26][C:27]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)=[O:28])[C:9]([NH:11][CH:12]([C:15]([C:16]2[O:17][C:18]3[C:19]([N:24]=2)=[N:20][CH:21]=[CH:22][CH:23]=3)=[O:25])[CH2:13][CH3:14])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 22054011HCID 22054011, compoundHCID 22607107sodium thiosulfate NaHCO3

Product 1

HCID 22053959HCID 22053959, compound

Procedure

This amide was treated with Dess-Martin periodinane (237.6 mg, 0.48 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 95 mg of 2-cyclohexylmethyl-4-morpholin-4-yl-N-[1-(oxazolo[4,5-b]pyridine-2-carbonyl)-propyl]-4-oxo-butyramide; H1 NMR(DMSO-d): 8.72–8.68(1H, m), 8.6(111, d, J=5.2 Hz, NH), 8.4–8.34(1H, m), 7.68–7.59(1H, m), 5.2–4.96(1H, m), 3.5–3.45(8H, m), 2.58(1H, m), 2.5–2.4(1H, m), 2.45–2.15(1H, m), 2.05–1.9(1H, m), 1.85–1.65(2H, m), 1.6–1.4(5H, m), 1.3–1.2(1H, m), 1.25–1(4H, m), 0.97(3H, t); MS: 469.6(M−1), 471.4(M+1), 493.2(M+Na).

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-6edcfe09355a4a73b009f114b921e567
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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