Triacetoxyperiodinane → 2-Cyclohexylmethyl-n-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830195Notes

Reaction equation

HRID 1830195 reaction equation
[CH:1]1([CH2:7][CH:8]([CH2:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[C:9]([NH:11][CH:12]([CH:16]([C:18]2[O:19][C:20]([CH2:23][CH3:24])=[N:21][N:22]=2)[OH:17])[CH2:13][CH2:14][CH3:15])=[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-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>>[CH:1]1([CH2:7][CH:8]([CH2:25][C:26]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[O:27])[C:9]([NH:11][CH:12]([C:16]([C:18]2[O:19][C:20]([CH2:23][CH3:24])=[N:21][N:22]=2)=[O:17])[CH2:13][CH2:14][CH3:15])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 18470521Sodium bicarbonate sodium sulfiteHCID 220540862-cyclohexylmethyl-N-{1-[(5-ethyl-[1,3,4]oxadiazol-2-yl)-hydroxy-methyl]-butyl}-4-morpholin-4-yl-4-oxo-butyramide

Product 1

HCID 220539852-Cyclohexylmethyl-n-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide

Procedure

This amide was treated with Dess-Martin periodinane (239 mg, 0.48 mmol) at room temperature. After stiffing 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 65 mg of 2-cyclohexylmethyl-N-[1-(5-ethyl-[1,3,4]oxadiazole-2-carbonyl)-butyl]-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR (DMSO-d): 8.6, 8.51(11H, dd, J=6.8 Hz, J=5.6 Hz, NH, diastereomeric), 4.98(−4.88 (1H, m), 3.6–3.25(8H, m), 3–2.9(2H, q, J=7.6 Hz), 2.9–2.75(1H, m), 2.5–2.4(1H, m), 2.3–2.1(1H, m), 1.9–1.7(2H, m), 1.7–1.4(7H, m), 1.4–1.2(2H, m), 1.28(3H, t), 1.2–1(6H, m), 0.88(3H, t); MS: 461.4(M−1), 463.4(M+1), 485.4(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-60a92c94734740359d4c48d1a79e2d11
Source dataset
uspto-grants-2006_06
Patent number
US07064123B1

Reaction notes

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