1-butylsulfinylbutane

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: A mixture of 0.742 g of (2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxirane (obtained by analogy with the method disclosed in WO 99/65895 but starting from the butyl sulfoxide instead of the methyl sulfoxide and using (S)-(+)-glycidyl nosylate; [α]D=+1.9 (c=1%, MeOH)) (2.06 mmol) and of 0.666 g of ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate hydrochloride (2.18 mmol) in ethanol (25 ml) is heated to reflux overnight. The solvent is evaporated under reduced pressure and the product obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (95/5/0.5) mixture. The title product is obtained in the form of a yellow oil (0.730 g, 53%). obtained by analogy with the method to reflux overnight The solvent is evaporated under reduced pressure the product obtained is purified by flash chromatography, elution

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

実験手順: A mixture of 0.742 g of (2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxirane (obtained by analogy with the method disclosed in WO 99/65895 but starting from the butyl sulfoxide instead of the methyl sulfoxide and using (S)-(+)-glycidyl nosylate; [α]D=+1.9 (c=1%, MeOH)) (2.06 mmol) and of 0.666 g of ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate hydrochloride (2.18 mmol) in ethanol (25 ml) is heated to reflux overnight. The solvent is evaporated under reduced pressure and the product obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (95/5/0.5) mixture. The title product is obtained in the form of a yellow oil (0.730 g, 53%). obtained by analogy with the method to reflux overnight The solvent is evaporated under reduced pressure the product obtained is purified by flash chromatography, elution

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

実験手順: 0.055 g (0.5 mmol) of uracil was weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with trifluoromethyl iodide. The following materials were added thereinto: 2.5 ml of dibutyl sulfoxide, 0.027 ml of concentrated sulfuric acid, 0.1 ml of a 30% hydrogen peroxide aqueous solution and 0.15 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40° C. to 50° C. Thereafter, the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 0.19%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. placed in a two-neck flask The following materials were added rose up in the range of from 40° C. to 50° C

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

実験手順: The title compound 5 was synthesized similar to the procedure described in Example 1 for compound 3 using dibutyl sulfoxide instead of DMSO. After column chromatography, 227 mg (86.3% yield, 99.4 purity) of compound 5 was isolated as an off-white solid as a mixture of two epimers in a 95.4:4.6 ratio. The title compound 5 was synthesized similar to the procedure

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

実験手順: The title compound 5 was synthesized similar to the procedure described in Example 1 for compound 3 using dibutyl sulfoxide instead of DMSO. After column chromatography, 227 mg (86.3% yield, 99.4 purity) of compound 5 was isolated as an off-white solid as a mixture of two epimers in a 95.4:4.6 ratio. The title compound 5 was synthesized similar to the procedure

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

実験手順: A mixture of 0.742 g of (2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxirane (obtained by analogy with the method disclosed in WO 99/65895 but starting from the butyl sulfoxide instead of the methyl sulfoxide and using (S)-(+)-glycidyl nosylate; [α]D=+1.9 (c=1%, MeOH)) (2.06 mmol) and of 0.666 g of ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate hydrochloride (2.18 mmol) in ethanol (25 ml) is heated to reflux overnight. The solvent is evaporated under reduced pressure and the product obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (95/5/0.5) mixture. The title product is obtained in the form of a yellow oil (0.730 g, 53%). obtained by analogy with the method to reflux overnight The solvent is evaporated under reduced pressure the product obtained is purified by flash chromatography, elution

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

実験手順: A mixture of 0.742 g of (2S)-2-{[4-(benzyloxy)-3-(butylsulfinyl)phenoxy]methyl}oxirane (obtained by analogy with the method disclosed in WO 99/65895 but starting from the butyl sulfoxide instead of the methyl sulfoxide and using (S)-(+)-glycidyl nosylate; [α]D=+1.9 (c=1%, MeOH)) (2.06 mmol) and of 0.666 g of ethyl trans-2-[4-(4-aminocyclohexyl)phenoxy]-2,2-dimethylacetate hydrochloride (2.18 mmol) in ethanol (25 ml) is heated to reflux overnight. The solvent is evaporated under reduced pressure and the product obtained is purified by flash chromatography, elution being carried out with a methylene chloride/methanol/aqueous ammonia (95/5/0.5) mixture. The title product is obtained in the form of a yellow oil (0.730 g, 53%). obtained by analogy with the method to reflux overnight The solvent is evaporated under reduced pressure the product obtained is purified by flash chromatography, elution

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 0.11 g (1.0 mmol) of uracil was weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with trifluoromethyl iodide. The following materials were added thereinto: 5.0 ml of dibutyl sulfoxide, 0.053 ml of concentrated sulfuric acid, 0.2 ml of a 30% hydrogen peroxide aqueous solution and 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. The mixture was stirred at 40 to 50° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 0.2%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. placed in a 50 ml two-neck flask equipped with a magnetic rotor The following materials were added the resulting solution was cooled to room temperature

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

実験手順: 0.055 g (0.5 mmol) of uracil was weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with trifluoromethyl iodide. The following materials were added thereinto: 2.5 ml of dibutyl sulfoxide, 0.027 ml of concentrated sulfuric acid, 0.1 ml of a 30% hydrogen peroxide aqueous solution and 0.15 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40° C. to 50° C. Thereafter, the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 0.19%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. placed in a two-neck flask The following materials were added rose up in the range of from 40° C. to 50° C

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

実験手順: The title compound 5 was synthesized similar to the procedure described in Example 1 for compound 3 using dibutyl sulfoxide instead of DMSO. After column chromatography, 227 mg (86.3% yield, 99.4 purity) of compound 5 was isolated as an off-white solid as a mixture of two epimers in a 95.4:4.6 ratio. The title compound 5 was synthesized similar to the procedure