1,2-Dichloroethane → (3S)-N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide

HRID 1366539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1366539
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@H:6]([C:15]([OH:17])=O)[CH2:5][O:4][CH2:3]1.[CH3:18][NH:19][CH3:20].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CN1CCOCC1>C1COCC1>[CH3:18][N:19]([CH3:20])[C:15]([C@@H:6]1[CH2:5][O:4][CH2:3][C:2](=[O:1])[N:7]1[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:17]

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 674DimethylamineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 13543372(3S)-5-Oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid

Produkt 1

HCID 66936283(3S)-N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (3S)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (1.5 g, 6.4 mmol) (J. Chem. Soc., Perkin Trans. 1, 1985, 2577-2580) in THF (50 mL) was added dimethylamine (3.8 mL, 7.6 mmol, 2M in THF), EDC (1.46 g, 7.7 mmol), HOAt (1.06 g, 7.7 mmol) and NMM (3.5 mL, 30 mmol). The reaction mixture was stirred overnight and the THF was evaporated, replacing it with EtOAc. 1 M HCl was added and the phases were separated. The aqueous layer was extracted twice with EtOAc and the combined organics were dried over sodium sulfate. Concentration in vacuo yielded (3S)—N,N-dimethyl-5-oxo-4-(phenylmethyl)-3 morpholinecarboxamide, which was purified by RP-HPLC. LCMS: (M+H)+: 263.1.

Aufarbeitung

  1. customthe THF was evaporated
  2. addition1 M HCl was added
  3. customthe phases were separated
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. dry with materialthe combined organics were dried over sodium sulfate
  6. concentrationConcentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-efd6c4c1571942a4a26c01b228a9ebaa
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893056B2

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