Benzylamine → HCID 68540058, compound

Participants

Reaction Conditions

Reaction Steps

t-Butyl 2-(4-(4-methoxybenzyl)-2,2-dioxo-(1,2,3) oxathiazolidin-3-yl)-3-methylbutyrate (1.0 g; 2.5 mmol) was dissolved in acetonitrile (15 ml). Cs2CO3 (1.63 g; 5 mmol) and benzylamine (0.5 ml; 4.5 mmol) were added, The reaction mixture was stirred at 55° C. for 4 h. It was then allowed to reach RT, and the reaction mixture was filtered through a clarifying layer. The residue was washed with acetonitrile. The filtrate was concentrated and taken up in CH2Cl2 (10 ml). Aqueous H2SO4 (20%; 5 ml) was added, and the mixture was stirred at RT for 1.5 h. The phases were then separated, the aqueous phase was extracted with CH2Cl2 (2×), and the combined organic phases were dried over Na2SO4 and concentrated in a rotary evaporator. The crude product was stirred with CH2Cl2/CH3CN/Et2O and concentrated. t-Butyl 2-(2-benzylamino-1-(4-methoxybenzyl)ethylamino)-3-methylbutyrate (1.15 g; 2.5 mmol) was obtained as a yellowish foam. MS: 427.20 (M+H); Rt: 1.42 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Provenance & Evidence