tert-butyl 2-anilinoacetate

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%). The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%). The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%). The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%) The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%) The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, II mmol) in pyridine (10 mL) at 0 C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1,100%). The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil

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

実験手順: Working as in Example 15, but starting with (RS)-2-[3-(3-methylphenyl)ureido]-3-phenylpropanoic acid (4.8 g) and tert-butyl anilinoacetate (3.3 g) in anhydrous 1,2-dichloroethane (300 cc) and thionyl chloride (1.16 cc), and recrystallizing successively in diethyl ether and then in isopropanol, tert-butyl (RS)-N-{2-[3-(3-methylphenyl)ureido]-3-phenylpropionyl}-N-phenylglycinate (3.2 g), m.p. 198° C., is obtained. recrystallizing successively in diethyl ether

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

実験手順: A suspension of (RS)-2-[3-(3-methylphenyl)ureido]-4-(methylthio)butanoic acid (4.5 g) and tert-butyl anilinoacetate (3.3 g) in anhydrous 1,2-dichloroethane (300 cc) is heated to reflux until a solution is obtained. Thionyl chloride (1.16 cc) is then added, refluxing being maintained until the gaseous evolution has ceased. The reaction mixture is then poured into a saturated aqueous sodium bicarbonate solution (100 cc) and the organic phase is washed with water (100 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. The oily residue obtained is purified by chromatography on silica gel (0.04-0.063 mm; 350 g) contained in a column 5 cm in diameter [eluant: methylene chloride/methanol (98:2 by volume)], using an excess pressure of 40 kPa of nitrogen and collecting 100-cc fractions. Fractions 12 to 28 are combined and concentrated to dryness under reduced pressure (2.7 kPa) at 40° C. By recrystallization of the residue thereby obtained in diethyl ether, tert-butyl (RS)-N-{2-[3-(3-methylphenyl)ureido]-4-methylthiobutyryl}-N-phenylglycinate (2.8 g), m.p. 142° C., is obtained. is heated to reflux until a solution is obtained refluxing being maintained until the gaseous evolution the organic phase is washed with water (100 cc) dried over magnesium sulphate concentrated to dryness under reduced pressure (2.7 kPa) at 40° C The oily residue obtained is purified by chromatography on silica gel (0.04-0.063 mm; 350 g) collecting 100-cc fractions concentrated to dryness under reduced pressure (2.7 kPa) at 40° C By recrystallization of the residue thereby obtained in diethyl ether

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

実験手順: N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl chloride (3.00 g, 10 mmol) in dichloromethane (20 mL) was added dropwise to a solution of tert-butyl-N-phenylglycinate (2.3 mg, 11 mmol) in pyridine (10 mL) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The reaction was diluted with H2O (100 mL) and EtOAc (150 mL). The organic phase was separated and washed successively with citric acid (10%, 2×100 mL) and brine (100 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow viscous oil. Column chromatography (SiO2, 20-50% EtOAc in petroleum ether) gave tert-butyl N-[(4S)-3-benzyloxycarbonyl-5-oxo-oxazolidin-4-yl-acetyl]-N-phenylglycinate as a white foam. MS (APCI) m/z 467 (M+−1, 100%). The organic phase was separated washed successively with citric acid (10%, 2×100 mL) and brine (100 mL) dried (MgSO4) filtered concentrated in vacuo to give a yellow viscous oil