methyl 3-(2-aminoethylsulfanyl)propanoate;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1′-Carbonyldiimidazole (0.36 g, 2.2 mmol) was added to a solution of 5-phenyl-penta-2E,4E-dienoic acid (1/1) (0.35 g, 2 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for 1 hour at ambient temperature. To the mixture triethylamine (0.30 g 3.0 mmol) and methyl 3-(2-amino-ethylsulfanyl)-propionate hydrochloride (2e) (2.2 mmol) were added and the resultant suspension was stirred for 6 hours at ambient temperature. The solvent was removed under reduced pressure, to the residue water (15 ml) was added and the precipitate was filtered off, washed with water and dried, to give the title product. Yield 67%, m.p. 58-60° C. 1H NMR (90 MHz, DMSO-d6) δ: 2.54-2.89 (6H, m, CH2); 2.96-3.45 (2H, m, CH2); 3.61 (3H, s, CH3); 6.14 (1H, d, J=14.5 Hz, CH); 6.81-7.16 (2H, m, CH—CH); 7.11-7.69 (6H, m, C6H5, CH); 8.18 (1H, t, J=5.4 Hz, NH). The solvent was removed under reduced pressure, to the residue water (15 ml) was added the precipitate was filtered off washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1,1′-Carbonyldiimidazole (0.36 g, 2.2 mmol) was added to a solution of 5-phenyl-penta-2E,4E-dienoic acid (1/1) (0.35 g, 2 mmol) in dry tetrahydrofuran (10 ml) and the obtained mixture was stirred for 1 hour at ambient temperature. To the mixture triethylamine (0.30 g 3.0 mmol) and methyl 3-(2-amino-ethylsulfanyl)-propionate hydrochloride (2e) (2.2 mmol) were added and the resultant suspension was stirred for 6 hours at ambient temperature. The solvent was removed under reduced pressure, to the residue water (15 ml) was added and the precipitate was filtered off, washed with water and dried, to give the title product. Yield 67%, m.p. 58-60° C. 1H NMR (90 MHz, DMSO-d6) δ: 2.54-2.89 (6H, m, CH2); 2.96-3.45 (2H, m, CH2); 3.61 (3H, s, CH3); 6.14 (1H, d, J=14.5 Hz, CH); 6.81-7.16 (2H, m, CH—CH); 7.11-7.69 (6H, m, C6H5, CH); 8.18 (1H, t, J=5.4 Hz, NH). The solvent was removed under reduced pressure, to the residue water (15 ml) was added the precipitate was filtered off washed with water dried