Triethylamine → N-methoxy-N-methyl-3-oxocyclobutanecarboxamide

HRID 707350Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 707350
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.Cl.[CH3:10][O:11][NH:12][CH3:13].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>ClCCl.O>[CH3:10][O:11][N:12]([CH3:13])[C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8]

Komponenten

8

Edukt 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 49133583-Oxocyclobutane-1-carboxylic acid

Produkt 1

HCID 86634348N-methoxy-N-methyl-3-oxocyclobutanecarboxamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3-oxo-cyclobutanecarboxylic acid (2.28 g, 20.0 mmol), O,N-dimethyl-hydroxylamine hydrochloride (1.94 g, 20.0 mmol), 1-hydroxybenzotriazole (2.99 g, 22.0 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (4.22 g, 22.0 mmol) and triethylamine (4.04 g, 40.0 mmol) in dichloromethane (50 mL) was stirred at room temperature for 24 hours. The mixture was diluted with water (30 mL), and extracted with dichloromethane (2×30 mL). The combined organic extracts were washed with water (20 mL) and brine (20 mL), and dried over sodium sulfate. The filtrate was evaporated in vacuo and the residue was purified by silica chromatography to provide N-methoxy-N-methyl-3-oxocyclobutanecarboxamide (2.68 g, 17.0 mmol, yield: 85%).

Aufarbeitung

  1. extractionextracted with dichloromethane (2×30 mL)
  2. washThe combined organic extracts were washed with water (20 mL) and brine (20 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue was purified by silica chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f645a08471ea44f3b558b89226ec050e
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174992B2

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