Triethylamine → 2-cyclopropyl-N-methoxy-N-methylacetamide

HRID 1426001

Reaktionsgleichung

Reaktionsgleichung von HRID 1426001
F[P-](F)(F)(F)(F)F.[N:8]1([O:17][C:18](N(C)C)=[N+](C)C)[C:12]2N=CC=CC=2N=N1.CONC.C(N(CC)CC)C.[CH:36]1([CH2:39][C:40]([OH:42])=O)[CH2:38][CH2:37]1>C(Cl)Cl>[CH:36]1([CH2:39][C:40]([N:8]([O:17][CH3:18])[CH3:12])=[O:42])[CH2:38][CH2:37]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14232N,O-DimethylhydroxylamineHCID 138440Cyclopropaneacetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 224737662-cyclopropyl-N-methoxy-N-methylacetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2-(7-Aza-1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (19.0 g), N-methoxymethanamine (5.0 g), and triethylamine (15.1 g) were added to a solution of 2-cyclopropylacetic acid (5.0 g) in CH2Cl2 (200 mL) at 0° C. The mixture was stirred at room temperature for 3 h. The reaction mixture was then washed with water and the aqueous washing phase was extracted with ethyl acetate (5×50 mL). The combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 20:1→5:1) to give the title compound. Yield: 4.1 g (58% of theory).

Aufarbeitung

  1. washThe reaction mixture was then washed with water
  2. extractionthe aqueous washing phase was extracted with ethyl acetate (5×50 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (petroleum ether/ethyl acetate 20:1→5:1)

Quellen und Nachweise

ORD-Eintrag
ord-01319bc990d94edda759efa56694d2e7
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933072B2

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