Dimethylformamide → HCID 66990718, Verbindung

HRID 2367365

Reaktionsgleichung

Reaktionsgleichung von HRID 2367365
C(Cl)(=O)C(Cl)=O.[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][O:17][CH:16]([C:20]([OH:22])=O)[CH2:15]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C=O)C.C(N(CC)CC)C.[NH2:35][CH2:36][C:37]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=1)=[O:38]>C(Cl)Cl.O>[CH3:46][O:45][C:42]1[CH:41]=[CH:40][C:39]([C:37](=[O:38])[CH2:36][NH:35][C:20]([CH:16]2[O:17][CH2:18][CH2:19][N:14]([CH2:13][C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:15]2)=[O:22])=[CH:44][CH:43]=1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 4128892-Amino-4'-methoxyacetophenoneHCID 27763534-Benzylmorpholine-2-carboxylic acid

Produkt 1

HCID 66990718HCID 66990718, VerbindungAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Oxalyl chloride (2.385 mL, 27.2 mmol) was added to a suspension of 4-(phenylmethyl)-2-morpholinecarboxylic acid (4.02 g, 18.16 mmol) and DMF (0.703 mL, 9.08 mmol) in CH2Cl2 (100 mL) at 0° C. in 10 minutes, and the reaction mixture was stirred at 25° C. for 2 hours. The mixture was concentrated, and the resulting residue was dissolved in CH2Cl2 (100 mL) and triethylamine (5.57 mL, 40.0 mmol). 2-Amino-1-[4-(methyloxy)phenyl]ethanone (3.0 g, 18.16 mmol) was added to the brown solution at 0° C., and the reaction mixture was stirred at 25° C. for 3 hours. Water (150 mL) was added to the reaction mixture, and the aqueous mixture was extracted with EtOAc (3×100 mL). The combined organic layers were dried (Na2SO4), filtered, and evaporated to afford the title compound (3.4 g) as a brown solid. LC-MS (ES) m/z=369 [M+H]+.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionthe resulting residue was dissolved in CH2Cl2 (100 mL)
  3. stirringthe reaction mixture was stirred at 25° C. for 3 hours
  4. extractionthe aqueous mixture was extracted with EtOAc (3×100 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-972a42a71db94f7792cd6b97db319f32
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697685B2

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