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

Participants

Reaction Conditions

Reaction Steps

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+ ]

Provenance & Evidence