2-methyl-2-nitropropan-1-ol

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: A mixed solution containing 46 g of 3-(p-amino-benzoyl)propionic acid hydrochloride, 25 g of 2-methyl-2-nitro-1-propanol, 1 g of benzyl triethyl ammonium chloride, 17 g of sodium hydroxide and 40 ml of water was heated under reflux for 6 hours. Then, 12 g of 2-methyl-2-nitro-1-propanol was added, and the mixture was further heated under reflux for 18 hours. Then 20% HCl was added. The solution was acidified (pH 2). The crystals which precipitated were collected by filtration. The crystals were washed with water and recrystallized from tetrahydrofuran to give 51.6 g of 3-[4-(2-methyl-2-nitropropylamino)benzoyl]propionic acid. was heated under reflux for 6 hours the mixture was further heated under reflux for 18 hours The crystals which precipitated were collected by filtration The crystals were washed with water recrystallized from tetrahydrofuran

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

実験手順: A mixed solution containing 46 g of 3-(p-aminobenzoyl)propionic acid hydrochloride, 25 g of 2-methyl-2-nitro-1-propanol, 1 g of benzyl triethyl ammonium chloride, 17 g of sodium hydroxide and 40 ml of water was heated under reflux for 6 hours. Then, 12 g of 2-methyl-2-nitro-1-propanol was added, and the mixture was further heated under reflux for 18 hours. Then 20% HCl was added. The solution was acidified (pH 2). The crystals which precipitated were collected by filtration. The crystals were washed with water and recrystallized from tetrahydrofuran to give 51.6 g of 3-[4-(2-methyl-2-nitropropylamino)benzoyl]propionic acid. was heated under reflux for 6 hours the mixture was further heated under reflux for 18 hours The crystals which precipitated were collected by filtration The crystals were washed with water recrystallized from tetrahydrofuran

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

実験手順: A mixed solution containing 46 g of 3-(p-aminobenzoyl)propionic acid hydrochloride, 25 g of 2-methyl-2-nitro-1-propanol, 1 g of benzyl triethyl ammonium chloride, 17 g of sodium hydroxide and 40 ml of water was heated under reflux for 6 hours. Then, 12 g of 2-methyl-2-nitro-1-propanol was added, and the mixture was further heated under reflux for 18 hours. Then 20% HCl was added. The solution was acidified (pH 2). The crystals which precipitated were collected by filtration. The crystals were washed with water and recrystallized from tetrahydrofuran to give 51.6 g of 3-[4-(2-methyl-2-nitropropylamino)benzoyl]propionic acid. was heated under reflux for 6 hours the mixture was further heated under reflux for 18 hours The crystals which precipitated were collected by filtration The crystals were washed with water recrystallized from tetrahydrofuran

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

実験手順: To a suspension of 2-methyl-2-nitro-1-propanol (2.3975 g, 20.13 mmol) and Ag2O (4.6385 g, 20.02 mmol) in DMF (25 ml) was added benzyl bromide (2.65ml, 22.28 mmol) and stirred for 48 hours. The mixture was filtered and the filtrate was added to 5% KHSO4 aqueous solution, extracted three times with ethyl acetate/hexane=1/1 and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (toluene) to give the title compound (639.4 mg; 15%). The mixture was filtered the filtrate was added to 5% KHSO4 aqueous solution extracted three times with ethyl acetate/hexane=1/1 dried over MgSO4 The mixture was concentrated purified by silica gel chromatography (toluene)

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

実験手順: Acetic anhydride (0.34 ml, 3.60 mmol) was added to a solution of 2-methyl-2-nitro-1-propanol (375.4 mg, 3.15 mmol) and triethylamine (0.80 ml, 5.74 mmol) in dichloromethane (5 ml) and stirred for 2.5 hours. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=3/1) to give the title compound (467.8 mg; 92%). The mixture was concentrated purified by silica gel chromatography (hexane/ether=3/1)

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

実験手順: To a solution of 2-methyl-2-nitro-1-propanol (366.8 mg, 3.08 mmol) and LiBr (60.8 mg, 0.700 mmol) in dimethoxymethane (5 ml) was added p-toluenesulfonic acid hydrate (56.3 mg, 0.296 mmol) and stirred for 24 hours. The mixture was added to water and extracted three times with ethyl acetate and dried over MgSO4. The mixture was concentrated and purified by silica gel chromatography (hexane/ether=4/1) to give the title compound (382.7 mg; 76%). extracted three times with ethyl acetate dried over MgSO4 The mixture was concentrated purified by silica gel chromatography (hexane/ether=4/1)

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 mixed solution containing 46 g of 3-(p-aminobenzoyl)propionic acid hydrochloride, 25 g of 2-methyl-2-nitro-1-propanol, 1 g of benzyl triethyl ammonium chloride, 17 g of sodium hydroxide and 40 ml of water was heated under reflux for 6 hours. Then, 12 g of 2-methyl-2-nitro-1-propanol was added, and the mixture was further heated under reflux for 18 hours. Then 20% HCl was added. The solution was acidified (pH 2). The crystals which precipitated were collected by filtration. The crystals were washed with water and recrystallized from tetrahydrofuran to give 51.6 g of 3-[4-(2-methyl-2-nitropropylamino)benzoyl]propionic acid. was heated under reflux for 6 hours the mixture was further heated under reflux for 18 hours The crystals which precipitated were collected by filtration The crystals were washed with water recrystallized from tetrahydrofuran

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

実験手順: A mixture of γ-(p-aminobenzoyl)butyric acid hydrochloride (349.5 g), 2-methyl-2-nitro-1-propanol (222 g), sodium hydroxide (114.8 g), benzyltriethyl ammonium chloride (6.35 g) and water (1.5 liters) was refluxed for 40 hours. Concentrated hydrochloric acid (170 ml) was added to the reaction mixture to acidify it. The precipitated crystals were collected by filtration to give γ-[4-(2-methyl-2-nitropropylamino)benzoyl]butyric acid (364.46 g). was refluxed for 40 hours The precipitated crystals were collected by filtration