N-BOC-ethylenediamine → HCID 21480554, compound

Participants

Reaction Steps

A solution of fluorenylmethyl succinimidyl carbonate (31.0 g, 0.092 mol) in acetonitrile (300.0 ml) was slowly added to mono tert-butyloxycarbonylethylenediamine (10.0 g, 0.063 mol) dissolved in 10% aq. Na2CO3 (250 ml). Acetonitrile was evaporated and the product was extracted with ethyl acetate, organic phase was dried over Na2CO3, concentrated and the product was allowed to crystallize by adding petroleum ether. The product was collected on filter, washed with petroleum ether. Yield 20.0 g (84%). TLC petroleum ether--diethylether 88:12 Rf 0.64. NMR (300 MHz, DMSO-d6, 25° C.) d: 1.37 (s, 9H, tBu), 2.99 (m, 4H, CH2CH2), 4.20-4.29 (m, 3H, Fmoc OCH2CH--), 6.76 (t, 1H, NH), 7.25 (t, 1H, NH), 7.33-7.89 (m, 8H, Fmoc). M.p. 146°-148° C.

Provenance & Evidence