Triacetoxyperiodinane → n-[1-(Benzooxazole-2-carbonyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide

HRID 1830191Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1830191
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([OH:34])[CH:11]([NH:14][C:15](=[O:33])[CH:16]([CH2:26][CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[CH2:12][CH3:13].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:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:11]([NH:14][C:15](=[O:33])[CH:16]([CH2:26][CH:27]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32]1)[CH2:17][C:18]([N:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)=[O:19])[CH2:12][CH3:13])=[O:34]

Komponenten

4

Edukt 3

HCID 159087TriacetoxyperiodinaneHCID 22054056N-[1-(benzooxazol-2-yl-hydroxy-methyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramideHCID 22607107sodium thiosulfate NaHCO3

Produkt 1

HCID 22054058n-[1-(Benzooxazole-2-carbonyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide

Versuchsvorschrift

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 76 mg of N-[1-(benzooxazole-2-carbonyl)-propyl]-2-cyclohexylmethyl-4-morpholin-4-yl-4-oxo-butyramide; H1 NMR(DMSO-d): 8.49(1H, d, J=5.2 Hz, NH), 7.96(11H, d, J=7.6Hz), 7.86(111, d, J=8.4), 7.6(1H, m), 7.5(1H, m), 5.14–5.04(1H, m), 3.6–3.25(8H, m), 2.9–2.75(1H, m), 2.5–2.4(1H, m), 2.25–2.15(1H, m), 2–1.8(1H, m), 1.8–1.7(2H, m), 1.7–1.6(1H, m), 1.6–1.4(5H, m), 1.35–1.2(1H, m), 1.21–1(4H, m), 0.96(3H, t); MS: 468.6(M−1), 470.5(M+1), 492.3(M+Na).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8bc8f005854d4f0b985ef000e169ca9a
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07064123B1

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