ethyl 2-amino-3-sulfanylpropanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Sodium (0.075 mol) was added portionwise to ethanol (50 ml) under N2 atmosphere and this mixture was stirred until complete dissolution. Ethyl 2-amino-3-mercaptopropanoate (0.075 mol) was added and the mixture was stirred for 2 hours at RT. The solvent was evaporated, THF (50 ml) was added to the residue, and a solution of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.015 mol) in THF (50 ml) was added. 1,8-diazabicyclo[5.4.0]undec-7-ene (0.03 mol) was added and the resulting reaction mixture was stirred overnight at RT. The solvent was evaporated. The residue was stirred in water and extracted with CH2Cl2. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. This fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH2OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off, washed and dried, yielding (±)-ethyl α-[[[(4-chlorophenyl)[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]methyl]thio]methyl]glycine (compound 95). the mixture was stirred for 2 hours at RT The solvent was evaporated THF (50 ml) was added to the residue the resulting reaction mixture was stirred overnight at RT The solvent was evaporated The residue was stirred in water extracted with CH2Cl2 The organic layer was separated washed with water dried filtered the solvent was evaporated This fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH2OH 97/3) The pure fractions were collected the solvent was evaporated The residue was stirred in DIPE filtered off washed dried

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

実験手順: Sodium (0.075 mol) was added portionwise to ethanol (50 ml) under N2 atmosphere and this mixture was stirred until complete dissolution. Ethyl 2-amino-3-mercaptopropanoate (0.075 mol) was added and the mixture was stirred for 2 hours at RT. The solvent was evaporated, THF (50 ml) was added to the residue, and a solution of 2-[3-chloro-4-[chloro(4-chlorophenyl)methyl]phenyl]-1,2,4-triazine-3,5(2H,4H)-dione (0.015 mol) in THF (50 ml) was added. 1,8-diazabicyclo[5.4.0]undec-7-ene (0.03 mol) was added and the resulting reaction mixture was stirred overnight at RT. The solvent was evaporated. The residue was stirred in water and extracted with CH2Cl2. The organic layer was separated, washed with water, dried, filtered and the solvent was evaporated. This fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH2OH 97/3). The pure fractions were collected and the solvent was evaporated. The residue was stirred in DIPE, filtered off, washed and dried, yielding (±)-ethyl α-[[[(4-chlorophenyl)[2-chloro-4-(4,5-dihydro-3,5-dioxo-1,2,4-triazin-2(3H)-yl)phenyl]methyl]thio]methyl]glycine (compound 95). the mixture was stirred for 2 hours at RT The solvent was evaporated THF (50 ml) was added to the residue the resulting reaction mixture was stirred overnight at RT The solvent was evaporated The residue was stirred in water extracted with CH2Cl2 The organic layer was separated washed with water dried filtered the solvent was evaporated This fraction was purified by HPLC over silica gel (eluent: CH2Cl2/CH2OH 97/3) The pure fractions were collected the solvent was evaporated The residue was stirred in DIPE filtered off washed dried

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

実験手順: To 16.25 g (125 mmol) of 2,5-dimethoxy-2,5-dihydrofuran and 23.20 g (125 mmol) of ethyl 2-amino-3-mercaptopropanoate in 100 ml dry acetonitrile was added approximately 0.15 g of tosyl chloride. The mixture was stirred 1 hour at room temperature under nitrogen during which time complete solution was attained which became very dark. The mixture was concentrated in vacuo, taken up in ethyl acetate, then extracted with aqueous NaHCO3 solution followed by saturated NaCl solution. The organic portion was dried over MgSO4, filtered then concentrated to 50 ml. The concentrate was then chromatographed to give 8.35 g (31.0%) of the title compound as a dark oil. The mixture was concentrated in vacuo extracted with aqueous NaHCO3 solution The organic portion was dried over MgSO4 filtered then concentrated to 50 ml The concentrate was then chromatographed