Triethylamine → HCID 58504731, Verbindung

HRID 2367335

Reaktionsgleichung

Reaktionsgleichung von HRID 2367335
[C:1]1([CH2:7][N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]([OH:16])=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[NH2:23][CH2:24][C:25]([C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=1)=[O:26].C(N(CC)CC)C>C(Cl)Cl.O.CN(C=O)C>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([C:25](=[O:26])[CH2:24][NH:23][C:14]([CH:10]2[O:11][CH2:12][CH2:13][N:8]([CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:9]2)=[O:16])=[CH:32][CH:31]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 21637HCID 21637, VerbindungHCID 65578Oxalyl chlorideHCID 27763534-Benzylmorpholine-2-carboxylic acid

Produkt 1

HCID 58504731HCID 58504731, VerbindungAusbeute 125,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of 4-(phenylmethyl)-2-morpholinecarboxylic acid (1.61 g, 7.28 mmol) and DMF (0.1 mL) in CH2Cl2 (70 mL) was added oxalyl chloride (0.956 mL, 10.92 mmol) at 25° C. The mixture was stirred at this temperature for 1 hour and the mixture turned clear. The solvent and excess of oxalyl chloride were removed in vacuo, and the resulting residue was dissolved in CH2Cl2 (70 mL). 2-Amino-1-(4-chlorophenyl)ethanone (1.5 g, 7.28 mmol) and triethylamine (4.06 mL, 29.1 mmol) were added, and the resulting mixture was stirred overnight. Water (80 mL) was added to quench the reaction. The organic layer was separated and the aqueous layer was extracted with CH2Cl2 (2×80 mL). The combined organics were washed with sat. NaHCO3 aq. (80 mL), then brine (2×80 mL), dried (MgSO4), and evaporated to get 3.4 g yellow residue, which was chromatographed (EtOAc-petroleum ether, 1:1) to afford the title compound (2.5 g). LC-MS (ES) m/z=373 [M+H]+.

Aufarbeitung

  1. customThe solvent and excess of oxalyl chloride were removed in vacuo
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (70 mL)
  3. stirringthe resulting mixture was stirred overnight
  4. customto quench
  5. customthe reaction
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with CH2Cl2 (2×80 mL)
  8. washThe combined organics were washed with sat. NaHCO3 aq. (80 mL)
  9. dry with materialbrine (2×80 mL), dried (MgSO4)
  10. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2117ddf72c944496b061ad78302a4f5a
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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