Ethanol → Ethylenediaminium N,N'-diacetyl-L-cystinate

HRID 399732

Reaktionsgleichung

[C:1]([NH:4][C@H:5]([C:18]([OH:20])=[O:19])[CH2:6][S:7][S:8][CH2:9][C@H:10]([NH:14][C:15](=[O:17])[CH3:16])[C:11]([OH:13])=[O:12])(=[O:3])[CH3:2].[CH2:21]([NH2:24])[CH2:22][NH2:23].C(O)C>O>[CH2:21]([NH3+:24])[CH2:22][NH3+:23].[C:15]([NH:14][C@H:10]([C:11]([O-:13])=[O:12])[CH2:9][S:8][S:7][CH2:6][C@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:18]([O-:20])=[O:19])(=[O:17])[CH3:16]

Komponenten

Reaktionsbedingungen

Temperatur: 10 °C

Versuchsvorschrift

To N,N'-Diacetyl-L-cystine (30.9 mmol, 10 g) dissolved in 20 mL of water was added ethylenediamine (61.8 mmol, 3.73 g) and ethanol (30 mL). The solution was concentrated to a thick paste which was redissolved in 80 mL of ethanol. Crystallisation occurred after 2 hours stirring at 10° C. Filtration and drying gave 6.2 g (45%) of the title compound. Physical data: Mp 185.2°-192.4° C. 1 H-NMR (D2O) δ; 2.06 [6H, s, CH3 ], 2.96 [2H, dd, CH2S], 3.26 [2H, dd, CH2S], 3.28 [4H, s, H3N+CH2 CH2N30H3 ], 4.50 [2H, dd, CHN]. 13C-NMR (D2O) δ: 24.78; 39.99; 42.74; 56.98; 176.55; 179.82; Analysis: Calcd C: 37.5, H: 6.3, N: 14.6, S: 16.7. Found, C: 37.3, H: 6.8, N: 15.3, S: 15.2; MS m/z=385 [M(H2NCH2CH2NH2)H+ ]

Aufarbeitung

concentrationThe solution was concentrated to a thick paste which
dissolutionwas redissolved in 80 mL of ethanol
customCrystallisation
filtrationFiltration
customdrying

Quellen und Nachweise

ORD-Eintrag: ord-e4953668100040ff83bdb823701036af
Quelldatensatz: uspto-grants-1998_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05824681

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