tert-butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An ice cold 4 M solution of HCl in dioxane (4.73 mL, 18.9 mmol) was added to a solution of tert-butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate (Example 127 c, 500 mg, 1.89 mmol) in dichloromethane (10.2 mL). The mixture was stirred for 4 d at ambient temperature. Removal of the solvent in vacuo yielded the title compound (388 mg, quant.) as white solid which was used in the next step without further purification, MS (ESI) m/e=198.99 [M−H−]. Removal of the solvent in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Carbonyldiimidazole (520 mg, 3.21 mmol) was added to an ice cold solution of 3-tert-butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid (Example 127 b, 304 mg, 1.15 mmol) in DMF (1 mL). After 5 min. the mixture was warmed to ambient temperature and stirred for 2 h. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C. Stirring was continued for 12 h at ambient temperature. The reaction mixture was poured into 30 mL ice/water/1N HCl and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice/brine (20 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (197 mg, 65%) as white solid, MS (ESI) m/e=263.1 [M−H−]. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C Stirring was continued for 12 h at ambient temperature The reaction mixture was poured into 30 mL ice/water/1N HCl extracted with EtOAc (2×30 mL) The combined extracts were washed with ice/brine (20 mL) dried over Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Carbonyldiimidazole (520 mg, 3.21 mmol) was added to an ice cold solution of 3-tert-butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid (Example 127 b, 304 mg, 1.15 mmol) in DMF (1 mL). After 5 min. the mixture was warmed to ambient temperature and stirred for 2 h. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C. Stirring was continued for 12 h at ambient temperature. The reaction mixture was poured into 30 mL ice/water/1N HCl and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice/brine (20 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (197 mg, 65%) as white solid, MS (ESI) m/e=263.1 [M−H−]. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C Stirring was continued for 12 h at ambient temperature The reaction mixture was poured into 30 mL ice/water/1N HCl extracted with EtOAc (2×30 mL) The combined extracts were washed with ice/brine (20 mL) dried over Na2SO4 concentrated in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An ice cold 4 M solution of HCl in dioxane (4.73 mL, 18.9 mmol) was added to a solution of tert-butyl 4-carbamoyl-1,1-dioxo-1,3-thiazolidine-3-carboxylate (Example 127 c, 500 mg, 1.89 mmol) in dichloromethane (10.2 mL). The mixture was stirred for 4 d at ambient temperature. Removal of the solvent in vacuo yielded the title compound (388 mg, quant.) as white solid which was used in the next step without further purification, MS (ESI) m/e=198.99 [M−H−]. Removal of the solvent in vacuo

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Carbonyldiimidazole (520 mg, 3.21 mmol) was added to an ice cold solution of 3-tert-butoxycarbonyl-1,1-dioxo-1,3-thiazolidine-4-carboxylic acid (Example 127 b, 304 mg, 1.15 mmol) in DMF (1 mL). After 5 min. the mixture was warmed to ambient temperature and stirred for 2 h. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C. Stirring was continued for 12 h at ambient temperature. The reaction mixture was poured into 30 mL ice/water/1N HCl and extracted with EtOAc (2×30 mL). The combined extracts were washed with ice/brine (20 mL), dried over Na2SO4 and concentrated in vacuo to give the title compound (197 mg, 65%) as white solid, MS (ESI) m/e=263.1 [M−H−]. Gaseous NH3 was bubbled for 10 min through the solution while the temperature was kept below 20° C Stirring was continued for 12 h at ambient temperature The reaction mixture was poured into 30 mL ice/water/1N HCl extracted with EtOAc (2×30 mL) The combined extracts were washed with ice/brine (20 mL) dried over Na2SO4 concentrated in vacuo