3-[(4-氨基苯基)甲基]-1,3-噁唑烷-2-酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stiffing for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stiffing for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stiffing for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stiffing for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stiffing for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stiffing for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step. at reflux for 20 minutes is brought to 0° C. the emulsion obtained is filtered over Celite The filtrate is then extracted with DCM (2×300 ml) The organic phase obtained is washed with water and with saturated aqueous NaCl solution dried over sodium sulphate filtered The filtrate obtained is evaporated to dryness

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step. at reflux for 20 minutes is brought to 0° C. the emulsion obtained is filtered over Celite The filtrate is then extracted with DCM (2×300 ml) The organic phase obtained is washed with water and with saturated aqueous NaCl solution dried over sodium sulphate filtered The filtrate obtained is evaporated to dryness

反应条件: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stirring for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stirring for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step. at reflux for 20 minutes is brought to 0° C. the emulsion obtained is filtered over Celite The filtrate is then extracted with DCM (2×300 ml) The organic phase obtained is washed with water and with saturated aqueous NaCl solution dried over sodium sulphate filtered The filtrate obtained is evaporated to dryness

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl (methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stiffing for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stiffing for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stiffing for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step. at reflux for 20 minutes is brought to 0° C. the emulsion obtained is filtered over Celite The filtrate is then extracted with DCM (2×300 ml) The organic phase obtained is washed with water and with saturated aqueous NaCl solution dried over sodium sulphate filtered The filtrate obtained is evaporated to dryness

反应条件: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl(methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stirring for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of the compound obtained in Step A (0.244 mol) and SnCl2.2H2O (1.0 mol) in ethanol (300 ml) is stirred at reflux for 20 minutes. The solution is brought to 0° C. and made alkaline at pH=10-12 with aqueous sodium hydroxide solution; 500 ml of DCM are added and the emulsion obtained is filtered over Celite. The filtrate is then extracted with DCM (2×300 ml); the organic phases are combined. The organic phase obtained is washed with water and with saturated aqueous NaCl solution, dried over sodium sulphate and then filtered. The filtrate obtained is evaporated to dryness to yield the title product, which is used directly in the next Step. at reflux for 20 minutes is brought to 0° C. the emulsion obtained is filtered over Celite The filtrate is then extracted with DCM (2×300 ml) The organic phase obtained is washed with water and with saturated aqueous NaCl solution dried over sodium sulphate filtered The filtrate obtained is evaporated to dryness

反应条件: temp:-50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of the compound obtained in Step B (0.113 mol) in a mixture of CH3CN (200 ml) and THF (200 ml) at −60° C. there is added, dropwise, ethyl(methylsulphanyl)-acetate (0.136 mol) under a nitrogen atmosphere. tBuOCl (0.136 mol) is added dropwise to the reaction mixture over 20 minutes, keeping the temperature between −60° C. and −55° C. After stirring for one hour at −50° C., triethylamine (0.152 mol) is added dropwise. The reaction mixture is brought to 0° C. and then aqueous 3M HCl solution (580 ml) is added dropwise. After stirring for 12 hours at ambient temperature, the organic phases are evaporated in vacuo and then the aqueous phase is extracted with DCM and the organic phases are combined. The organic phase obtained is washed with water and then with saturated aqueous NaCl solution. The organic phase is dried over sodium sulphate, filtered and evaporated to dryness. The product obtained is recrystallised from a mixture of ethyl ether/ethanol. The crystals obtained are filtered off, washed with ether and dried in vacuo at 40° C. to yield the title product, which is used directly in the next Step. there is added the temperature between −60° C. and −55° C is brought to 0° C. After stirring for 12 hours at ambient temperature the organic phases are evaporated in vacuo the aqueous phase is extracted with DCM The organic phase obtained is washed with water The organic phase is dried over sodium sulphate filtered evaporated to dryness The product obtained is recrystallised from a mixture of ethyl ether/ethanol The crystals obtained are filtered off washed with ether dried in vacuo at 40° C.