Bis(2-chloroethyl)ethylamine → HCID 86667916, Verbindung

HRID 874581

Reaktionsgleichung

Reaktionsgleichung von HRID 874581
Cl.[NH2:2][C@@H:3]([CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4]([O:6][CH3:7])=[O:5].Cl[CH2:18][CH2:19][N:20]([CH2:23][CH2:24]Cl)[CH2:21][CH3:22]>C(N(CC)C(C)C)(C)C>[C:13]([O:12][C:10]([NH:9][CH2:8][C@H:3]([N:2]1[CH2:22][CH2:21][N:20]([CH2:23][CH3:24])[CH2:19][CH2:18]1)[C:4]([O:6][CH3:7])=[O:5])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 10848Bis(2-chloroethyl)ethylamineHCID 18334328methyl (2S)-2-amino-3-{[(tert-butoxy)carbonyl]amino}propanoate hydrochloride

Produkt 1

HCID 86667916HCID 86667916, VerbindungAusbeute 40,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 81531DiisopropylethylamineLösungsmittel

Versuchsvorschrift

A solution of 5.0 g (19.6 mmol) of commercial methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride and 3.3 g (19.6 mmol) of bis(2-chloroethyl)ethylamine in 50 ml of N,N-diisopropylethylamine is heated at 127° C. for 5 h. After evaporation of a maximum amount of diisopropylethylamine, the reaction medium is diluted with ethyl acetate and washed with an aqueous solution of sodium hydroxide having a concentration of 1N. The organic phase obtained is then washed with water, dried over magnesium sulfate, filtered and concentrated under vacuum. The crude product obtained is purified by chromatography on silica gel, elution being carried out with a 30/70 heptane/ethyl acetate mixture. 2.5 g (40%) of methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate are obtained in the form of an oil.

Aufarbeitung

  1. customAfter evaporation of a maximum amount of diisopropylethylamine
  2. additionthe reaction medium is diluted with ethyl acetate
  3. washwashed with an aqueous solution of sodium hydroxide having a concentration of 1N
  4. customThe organic phase obtained
  5. washis then washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customThe crude product obtained
  10. customis purified by chromatography on silica gel, elution

Quellen und Nachweise

ORD-Eintrag
ord-38cfb5e90a2341bab8cb438e7d52f29b
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08980897B2

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