Bis(2-chloroethyl)ethylamine → methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoate

HRID 1966121

Reaktionsgleichung

Reaktionsgleichung von HRID 1966121
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 86667916methyl (S)-3-tert-butoxycarbonylamino-2-(4-ethylpiperazin-1-yl)propanoateAusbeute 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-butoxycarbonylamino-propanoate 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-199a04bd1f6541679df7a3cf7b8fa495
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08420632B2

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