4-Morpholinepropanoic acid, methyl ester → 3-Morpholino-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide

HRID 1896748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1896748
[C:1]1([C:7]2[O:8][C:9]3[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][C:10]=3[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25](OC)=[O:26])[CH2:19][CH2:18]1.C[Al](C)C.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[O:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]([NH:16][C:13]2[CH:14]=[CH:15][C:9]3[O:8][C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[N:11][C:10]=3[CH:12]=2)=[O:26])[CH2:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 1013734-Morpholinepropanoic acid, methyl esterHCID 516892Sodium BicarbonateHCID 7210592-Phenyl-1,3-benzoxazol-5-amineHCID 16682925Trimethylaluminum

Produkt 1

HCID 673319083-Morpholino-N-(2-phenylbenzo[d]oxazol-5-yl)propanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To 2-phenylbenzo[d]oxazol-5-amine (75 mg, 0.36 mmol) and methyl 3-morpholinopropanoate (63 μL, 0.39 mmol) in toluene (2.5 mL) was added a 2M solution of trimethylaluminum in toluene (0.22 mL, 0.43 mmol). The resulting solution was heated twice for 5 min at 160° C. in the microwave. After cooling, sodium bicarbonate solution was added and the aqueous layer was extracted with ethyl acetate. The organic layer was then washed with brine and the combined organic layers were dried over anhydrous MgSO4. After evaporation, the impurities were removed by filtering through on a plug of silica eluting with ethyl acetate/hexanes 50:50 v/v and the desired product was obtained by elution with methanol to afford 17.5 mg (14%) of the title compound (LCMS RT=5.54 min, MH+ 352.0)

Aufarbeitung

  1. temperatureAfter cooling
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe organic layer was then washed with brine
  4. dry with materialthe combined organic layers were dried over anhydrous MgSO4
  5. customAfter evaporation
  6. customthe impurities were removed
  7. filtrationby filtering through on a plug of silica eluting with ethyl acetate/hexanes 50:50 v/v

Quellen und Nachweise

ORD-Eintrag
ord-65df4c1dc796480bb495e12218559b3e
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518980B2

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