2-[2-(methylamino)ethoxy]acetic acid

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:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension is prepared of 8 g (60 mM) of 2-(2-methylaminoethoxy)acetic acid in 100 ml of chloroform and 20 ml of acetonitrile, and, at ambient temperature, 17 ml (120 mM) of triethylamine are added, then, dropwise, 7.63 ml (60 mM) of chlorotrimethylsilane. The mixture is agitated at 60° C. for 2 hours and then cooled to ambient temperature and 17 ml (120 mM) of triethylamine and then 16.48 g (60 mM) of 4-methoxy-2-(trifluoromethyl)benzenesulphonyl chloride in solution in 60 ml of chloroform, are added slowly. The reaction mixture is kept under agitation at 5° C. for 16 hours, and then concentrated under reduced pressure. The residue is taken up into 150 ml of dichloromethane and is treated with 40 ml of an N solution of hydrochloric acid. The organic phase is separated, washed with water, and then extracted with twice 120 ml of N sodium hydroxide. The basic aqueous phase is separated, washed with 100 ml of dichloromethane and then acidified with a 5N solution of hydrochloric acid. The precipitate formed is extracted with twice 80 ml of dichloromethane; the organic phase obtained is washed with water and then dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is crystallised in isopropyl ether, separated off and dried. 6.32 g of the compound sought after are thus obtained as a white solid (yield=28%). cooled to ambient temperature The reaction mixture is kept under agitation at 5° C. for 16 hours concentrated under reduced pressure is treated with 40 ml of an N solution of hydrochloric acid The organic phase is separated washed with water extracted with twice 120 ml of N sodium hydroxide The basic aqueous phase is separated washed with 100 ml of dichloromethane The precipitate formed is extracted with twice 80 ml of dichloromethane the organic phase obtained is washed with water dried over magnesium sulphate concentrated under reduced pressure The residue obtained is crystallised in isopropyl ether separated off dried

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

実験手順: [2-(Methylamino)ethoxy]acetic acid (Bull. Soc. Chim.; 1956, 1210) (130 mg, 0.98 mmol) was mixed with triethylamine (0.56 mL, 4 mmol) in dry DMF (2 mL). Methylchloroformate (185 mg, 1.95 mmol) was added and the mixture was stirred at room temperature for 20 minutes, then quenched with water. Aqueous HCl (2M) was added to adjust the pH to ˜2. Product was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil (100 mg), which was used without further purification. quenched with water Aqueous HCl (2M) was added Product was extracted with ethyl acetate the organic phase was dried over magnesium sulfate concentrated under reduced pressure

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

実験手順: [2-(Methylamino)ethoxy]acetic acid (Bull. Soc. Chim.; 1956, 1210) (130 mg, 0.98 mmol) was mixed with triethylamine (0.56 mL, 4 mmol) in dry DMF (2 mL). Methylchloroformate (185 mg, 1.95 mmol) was added and the mixture was stirred at room temperature for 20 minutes, then quenched with water. Aqueous HCl (2M) was added to adjust the pH to ˜2. Product was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil (100 mg), which was used without further purification. quenched with water Aqueous HCl (2M) was added Product was extracted with ethyl acetate the organic phase was dried over magnesium sulfate concentrated under reduced pressure

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A suspension is prepared of 8 g (60 mM) of 2-(2-methylaminoethoxy)acetic acid in 100 ml of chloroform and 20 ml of acetonitrile, and, at ambient temperature, 17 ml (120 mM) of triethylamine are added, then, dropwise, 7.63 ml (60 mM) of chlorotrimethylsilane. The mixture is agitated at 60° C. for 2 hours and then cooled to ambient temperature and 17 ml (120 mM) of triethylamine and then 16.48 g (60 mM) of 4-methoxy-2-(trifluoromethyl)benzenesulphonyl chloride in solution in 60 ml of chloroform, are added slowly. The reaction mixture is kept under agitation at 5° C. for 16 hours, and then concentrated under reduced pressure. The residue is taken up into 150 ml of dichloromethane and is treated with 40 ml of an N solution of hydrochloric acid. The organic phase is separated, washed with water, and then extracted with twice 120 ml of N sodium hydroxide. The basic aqueous phase is separated, washed with 100 ml of dichloromethane and then acidified with a 5N solution of hydrochloric acid. The precipitate formed is extracted with twice 80 ml of dichloromethane; the organic phase obtained is washed with water and then dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is crystallised in isopropyl ether, separated off and dried. 6.32 g of the compound sought after are thus obtained as a white solid (yield=28%). cooled to ambient temperature The reaction mixture is kept under agitation at 5° C. for 16 hours concentrated under reduced pressure is treated with 40 ml of an N solution of hydrochloric acid The organic phase is separated washed with water extracted with twice 120 ml of N sodium hydroxide The basic aqueous phase is separated washed with 100 ml of dichloromethane The precipitate formed is extracted with twice 80 ml of dichloromethane the organic phase obtained is washed with water dried over magnesium sulphate concentrated under reduced pressure The residue obtained is crystallised in isopropyl ether separated off dried

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

実験手順: [2-(Methylamino)ethoxy]acetic acid (Bull. Soc. Chim.; 1956, 1210) (130 mg, 0.98 mmol) was mixed with triethylamine (0.56 mL, 4 mmol) in dry DMF (2 mL). Methylchloroformate (185 mg, 1.95 mmol) was added and the mixture was stirred at room temperature for 20 minutes, then quenched with water. Aqueous HCl (2M) was added to adjust the pH to ˜2. Product was extracted with ethyl acetate, the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil (100 mg), which was used without further purification. quenched with water Aqueous HCl (2M) was added Product was extracted with ethyl acetate the organic phase was dried over magnesium sulfate concentrated under reduced pressure