Methylamine → 5-Nitrooxy-pentanoic acid methylamide

HRID 2201607Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2201607
[N+:1]([O:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O)([O-:3])=[O:2].[CH2:12]([N:14](CC)CC)C.ClC(OCC)=O.CN.S([O-])([O-])(=O)=O.[Na+].[Na+]>ClCCl>[CH3:12][NH:14][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][O:4][N+:1]([O-:3])=[O:2]

Komponenten

7

Edukt 5

HCID 6329MethylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 24436Sodium SulfateHCID 117884725-nitrooxypentanoic Acid

Produkt 1

HCID 716186675-Nitrooxy-pentanoic acid methylamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of compound 2 (1.60 g, 1.0 eq) in dry dichloromethane (20.0 mL) cooled to 0° C. was added triethylamine (1.70 mL, 1.2 eq) followed by ethyl chloroformate (1.10 mL, 1.1 eq). The reaction mixture was stirred at 0° C. for 45 minutes and 40% aqueous methyl amine (20.0 mL) was added. The solution was stirred from 0° C. to RT for 18 hours and sodium sulphate was added to dry the reaction mixture. The resulting mixture was filtered off and the filtrate was concentrated under vacuum. The residue was adsorbed on silica gel and purified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (15CV*)] affording compound 3 as a colourless liquid (0.84 g, yield=47%).

Aufarbeitung

  1. stirringThe solution was stirred from 0° C. to RT for 18 hours
  2. customto dry the reaction mixture
  3. filtrationThe resulting mixture was filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. custompurified by flash chromatography [Biotage®, dichloromethane/methanol 100/0→97/3 (15CV*)]

Quellen und Nachweise

ORD-Eintrag
ord-c928b5ee08bd4c14b6c44a42f20b721c
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365489B2

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