Trifluoroacetic acid → (4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide

HRID 919138

Reaktionsgleichung

Reaktionsgleichung von HRID 919138
[CH3:1][N:2]([CH2:26][CH2:27][NH:28]C(=O)OC(C)(C)C)[C:3](=[O:25])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24].C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+]>ClCCl>[NH2:28][CH2:27][CH2:26][N:2]([CH3:1])[C:3](=[O:25])[CH2:4][CH2:5]/[CH:6]=[CH:7]\[CH2:8]/[CH:9]=[CH:10]\[CH2:11]/[CH:12]=[CH:13]\[CH2:14]/[CH:15]=[CH:16]\[CH2:17]/[CH:18]=[CH:19]\[CH2:20]/[CH:21]=[CH:22]\[CH2:23][CH3:24]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 86639146HCID 86639146, Verbindung

Produkt 1

HCID 59193341(4Z,7Z,10Z,13Z,16Z,19Z)-N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamideAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of tert-butyl 2-((4Z,7Z,10Z,13Z,16Z,19Z)—N-methyldocosa-4,7,10,13,16,19-hexaenamido)ethylcarbamate (1.71 g, 3.5 mmol)) in dichloromethane (50 mL) at 0° C. was slowly added TFA (17 mL). The mixture was stirred (0° C., 2 h) basified to pH 10 with saturated aqueous Na2CO3 and extracted with EA (3×150 mL). The combined organic layers were dried over MgSO4 and concentrated under reduced pressure to afford (4Z,7Z,10Z,13Z,16Z,19Z)—N-(2-aminoethyl)-N-methyldocosa-4,7,10,13,16,19-hexaenamide (1.31 g, 97%) as a light yellow oil.

Aufarbeitung

  1. customat 0° C.
  2. extractionextracted with EA (3×150 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2620e57cfa024eebb369cf895bd9c22d
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09272984B2

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