4-Methylmorpholine → HCID 131722457, Verbindung

HRID 1532856

Reaktionsgleichung

Reaktionsgleichung von HRID 1532856
COC(=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][O:11][CH2:12][CH:13]2[CH2:17][CH2:16][O:15][CH2:14]2)=[CH:6][C:5]=1[C:18]1C=CC=CC=1.Cl.[NH2:26][C@H:27]([C:32]([O:34][CH3:35])=[O:33])[CH2:28][CH2:29][S:30][CH3:31].ON1C(=O)[C:41]2[CH:44]=[CH:45][CH:46]=[CH:47][C:40]=2N=N1.CN(C)CCCN=C=NCC.CN1CC[O:63]CC1>[Li+].[OH-].CO.C(OCC)(=O)C.C(OCC)(=O)C.CCCCCC.O>[CH3:35][O:34][C:32](=[O:33])[C@H:27]([CH2:28][CH:29]([C:18](=[O:63])[C:5]1[CH:4]=[CH:9][CH:8]=[C:7]([CH2:10][O:11][CH2:12][CH:13]2[CH2:17][CH2:16][O:15][CH2:14]2)[C:6]=1[C:40]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:41]=1)[S:30][CH3:31])[NH2:26]

Komponenten

10

Edukt 5

HCID 79724-MethylmorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 11435579L-Methionine, methyl ester, hydrochlorideHCID 702254664-(3-Tetrahydrofurylmethyloxymethyl)-2-phenylbenzoic acid methyl ester

Produkt 1

HCID 131722457HCID 131722457, VerbindungAusbeute 32,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittelHCID 23717829Lithium hydroxide methanolLösungsmittel

Versuchsvorschrift

A solution of the product of Example 287B (0.406 g, 1.15 mmol) in saturated LiOH-methanol (6 mL) was heated to reflux for 15 hours. The reaction mixture was cooled to ambient temperature and treated with H2O. The mixture was extracted with ether (3×). The ether extracts were discarded and the aqueous phase was made acidic with 3 M HCl. The mixture was extracted with ether (4×), and the organic extracts were dried (Na2SO4) and concentrated under reduced pressure. The resulting amber oil was dissolved in DMF (12 mL) and the solution was treated with L-methionine, methyl ester hydrochloride (0.459 g, 2.30 mmol), 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (0.957 g, 5.75 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.12 g, 5.75 mmol), and finally N-methylmorpholine (0.822 g, 8.05 mmol). The reaction mixture was stirred at ambient temperature for 60 hours, diluted with ethyl acetate (36 mL), and extracted with 2 N HCl (3×), followed by saturated aqueous NaHCO3 (3×) and brine. The organic phase was dried (MgSO4) and concentrated to provide a gold oil. Flash column chromatography (30% ethyl acetate-hexane) afforded the desired compound (0.172 g, 29%).

Aufarbeitung

  1. temperatureto reflux for 15 hours
  2. extractionThe mixture was extracted with ether (3×)
  3. extractionThe mixture was extracted with ether (4×)
  4. dry with materialthe organic extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe resulting amber oil was dissolved in DMF (12 mL)
  7. extractionextracted with 2 N HCl (3×)
  8. dry with materialThe organic phase was dried (MgSO4)
  9. concentrationconcentrated
  10. customto provide a gold oil

Quellen und Nachweise

ORD-Eintrag
ord-e3600e13dec442aba1b47985a848cd2e
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06204293B1

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