Nitrogen → [2-(5-Oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

HRID 1189376Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1189376
N#N.[C:3]([O:7][C:8](=[O:22])[NH:9][C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)([CH3:6])([CH3:5])[CH3:4].[H-].[Na+].[C:25]1([C:31]2[O:35][CH:34]=[N:33][C:32]=2[C:36](Cl)=[O:37])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C1COCC1.O>[C:3]([O:7][C:8](=[O:22])[N:9]([C:10]1[N:11]=[C:12]([CH2:15][CH2:16][CH2:17][CH2:18][C:19](=[O:21])[CH3:20])[O:13][CH:14]=1)[C:36]([C:32]1[N:33]=[CH:34][O:35][C:31]=1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:37])([CH3:6])([CH3:4])[CH3:5]

Komponenten

7

Edukt 4

HCID 947NitrogenHCID 24758Sodium hydrideHCID 27763005-Phenyl-1,3-oxazole-4-carbonyl chlorideHCID 67128525[2-(5-Oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester

Produkt 1

HCID 67128650[2-(5-Oxo-hexyl)-oxazol-4-yl]-(5-phenyl-oxazole-4-carbonyl)-carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of [2-(5-oxo-hexyl)-oxazol-4-yl]-carbamic acid tert-butyl ester (65 mg, 0.23 mL) in THF (2.0 mL) was added to a suspension of NaH (12 mg, 0.28 mmol) in THF (1.0 mL) at 0° C. The resulting suspension was stirred at 0° C. for 5 min and at rt for 30 min. It was cooled to 0° C. and treated dropwise with a solution of the above prepared 5-phenyl-oxazole-4-carbonyl chloride in THF (1.0 mL). The resulting suspension was stirred for 30 min at 0° C. followed by 16 h at rt. Water was then added and the aq. layer was extracted several time with EA. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1→2:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:1 hept-EA)=0.39. LC-MS-conditions 02: tR=1.06 min, [M+H]+=454.20.

Aufarbeitung

  1. temperatureIt was cooled to 0° C.
  2. additiontreated dropwise with a solution of the
  3. stirringThe resulting suspension was stirred for 30 min at 0° C.
  4. waitfollowed by 16 h at rt
  5. extractionthe aq. layer was extracted several time with EA
  6. dry with materialextracts were dried over Na2SO4
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification of the residue by FC (4:1→2:1 hept-EA)

Quellen und Nachweise

ORD-Eintrag
ord-4b131ee75e474db79fcde7bfb1244d5f
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674111B2

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