BENZYL N-(2-AMINOETHYL)CARBAMATE HYDROCHLORIDE

White crystalline powder

Preparation of 2-(((benzyloxy)carbonyl)amino)ethanaminium chloride Benzyl tert-butyl ethane-1, 2-diyldicarbamate (1.5 g, 6.3 mmol) in MeOH (10 mL) was treated with HCl/EtOAc (2 mL). The reaction was stirred at room temperature for 10 h and concentrated to give the title compound (1.0 g, 85percent yield).Solid Phase Synthetic protocol: A solution of N-(benzyloxycarbonyloxy)succinimide (ZOSu, 100 g, 401 mmol) in dichloromethane (500 ml) was added dropwise over 2 hours to a solution of 5 ethylenediamine (1, 189 ml, 2.81 mol) in dichloromethane (750 ml). After 30 minutes the suspension was filtered and solids washed with dichloromethane. The filtrate was evaporated to dryness and the residue diluted with toluene (1.00 L) and water (0.50 L). The resulting mixture was filtered and the filtrate was separated to afford two phases. The aqueous phase contained the product; therefore it was extracted with 10 dichloromethane (2 x 250 ml). All organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was diluted with toluene (750 ml) and extracted with 2 M aqueous hydrochloric acid (500 ml) and 1 M aqueous hydrochloric acid (100 ml). Acidic aqueous phases were combined and basified with a solution of sodium hydroxide (60.0 g, 1.50 mol) in water (90 ml). The resulting mixture 15 was extracted with dichloromethane (4 x 200 ml), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and diluted with hexanes (200 ml). 4 M Solution of hydrogen chloride in ether (100 ml, 400 mmol) was added to the solution, the resulting suspension was concentrated in vacuo and diluted with hexanes (1.00 L). The precipitated solid was filtered, washed with hexanes and dried in vacuo to give (2-amino20 ethyl)-carbamic acid benzyl ester hydrochloride as white powder. 25 Yield: 62.62 g (68percent). RF (Si02, dichloromethane/methanol 4: 1): 0.25 (free base). 1H NMR spectrum (300 MHz, Ac0D-d4, 80 °C, dH): 7.42-7.26 (m, 5 H); 5.16 (s, 2 H); 3.60 (t, J=5.7 Hz, 2 H); 3.32 (t, J=5.7 Hz, 2 H).A solution of N-(benzyloxycarbonyloxy)succinimide (ZOSu, 100 g, 401 mmol) in dichloromethane (500 mL) was added dropwise over 2 hours to a solution ofethylenediamine (1, 189 mL, 2.81 mol) in dichloromethane (750 mL). After 30 minutes the suspension was filtered and solids washed with dichloromethane. The filtrate was evaporated to dryness and the residue diluted with toluene (1.00 L) and water (0.50 L). The resulting mixture was filtered and the filtrate was separated to afford two phases. The aqueous phase contained the product; therefore it was extracted withdichloromethane (2 x 250 mL). All organic phases were combined, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was diluted with toluene (750 mL) and extracted with 2 M aqueous hydrochloric acid (500 mL) and 1 M aqueous hydrochloric acid (100 mL). Acidic aqueous phases were combined and basified with a solution of sodium hydroxide (60.0 g, 1.50 mol) in water (90 mL). The resulting mixture was extracted with dichloromethane (4 x 200 mL), dried over anhydrous sodium sulfate, filtered, concentrated in vacuo and diluted with hexanes (200 mL). 4 M Solution of hydrogen chloride in ether (100 mL, 400 mmol) was added to the solution, the resulting suspension was concentrated in vacuo and diluted with hexanes (1.00 L). Theprecipitated solid was filtered, washed with hexanes and dried in vacuo to give (2-amino- ethyl)-carbamic acid benzyl ester hydrochloride as white powder.Yield : 62.62 g (68percent).RF (Si02, dichloromethane/methanol 4: 1) : 0.25 (free base).1H NMR spectrum (300 MHz, AcOD-d4, 80 °C, dH) : 7.42-7.26 (m, 5 H); 5.16 (s, 2 H); 3.60 (t, J = 5.7 Hz, 2 H); 3.32 (t, J = 5.7 Hz, 2 H).

Molecular Weight:230.69
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:5
Exact Mass:230.0822054
Monoisotopic Mass:230.0822054
Topological Polar Surface Area:64.4
Heavy Atom Count:15
Complexity:168
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes