2-[(4-氟苯基)氨基]乙酸乙酯

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of ethyl glyoxylate (2.47 g, 0.024 mol) in 1,2-dichloroethane (30 mL) under argon at room temperature was treated succesively with 4-fluoroaniline (1.80 g, 0.016 mol), sodium triacetoxyborohydride (5.12 g, 0.024 mol) and acetic acid (1 mL). After stirring for two hours, the mixture was concentrated, dissolved in ethyl acetate and washed 5% sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic solution was concentrated and crystallized from ether/hexanes to give the title product (2.07 g, 65%) as a colorless solid, mp 72°-73° C. Analysis calculated for C10H12 FNO2 ·0.07 H2O: C, 60.54; H, 6.16; N, 7.06; F, 9.58. Found: C, 60.75; H, 6.15; N, 6.96; F, 9.13. the mixture was concentrated dissolved in ethyl acetate washed 5% sodium bicarbonate, water and brine The dried (anhydrous magnesium sulfate) organic solution was concentrated crystallized from ether/hexanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of ethyl glyoxylate (2.47 g, 0.024 mol) in 1,2-dichloroethane (30 mL) under argon at room temperature was treated succesively with 4-fluoroaniline (1.80 g, 0.016 mol), sodium triacetoxyborohydride (5.12 g, 0.024 mol) and acetic acid (1 mL). After stirring for two hours, the mixture was concentrated, dissolved in ethyl acetate and washed 5% sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic solution was concentrated and crystallized from ether/hexanes to give the title product (2.07 g, 65%) as a colorless solid, mp 72°-73° C. Analysis calculated for C10H12 FNO2 ·0.07 H2O: C, 60.54; H, 6.16; N, 7.06; F, 9.58. Found: C, 60.75; H, 6.15; N, 6.96; F, 9.13. the mixture was concentrated dissolved in ethyl acetate washed 5% sodium bicarbonate, water and brine The dried (anhydrous magnesium sulfate) organic solution was concentrated crystallized from ether/hexanes

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-((4-fluorophenyl)amino)acetate (1) (6.68 g, 33.9 mmol) in THF (84 mL) was added acetyl chloride (2.88 mL, 40.6 mmol) and the reaction was stirred overnight at room temperature. Water was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to yield ethyl 2-(N-(4-fluorophenyl)acetamido)acetate (2) as an orange solid. the reaction was extracted with ethyl acetate The combined organic layers were dried over sodium sulfate filtered concentrated in vacuo

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl bromoacetate (8.09 g, 48.4 mmol) was slowly added to a solution of 4-fluoroaniline (5.38 g, 48.4 mmol) and sodium acetate (5.16 g, 62.9 mmol) in ethanol (62 mL) and the mixture was heated at 80° C. for 2 h. Water was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes) to afford ethyl 2-((4-fluorophenyl)amino)acetate (1). the reaction was extracted with ethyl acetate The combined organic layers were dried over sodium sulfate filtered concentrated in vacuo The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes)

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Ethyl bromoacetate (8.09 g, 48.4 mmol) was slowly added to a solution of 4-fluoroaniline (5.38 g, 48.4 mmol) and sodium acetate (5.16 g, 62.9 mmol) in ethanol (62 mL) and the mixture was heated at 80° C. for 2 h. Water was added and the reaction was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes) to afford ethyl 2-((4-fluorophenyl)amino)acetate (1). the reaction was extracted with ethyl acetate The combined organic layers were dried over sodium sulfate filtered concentrated in vacuo The residue was purified by flash column chromatography on silica gel (0-20% EtOAc in hexanes)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of ethyl glyoxylate (2.47 g, 0.024 mol) in 1,2-dichloroethane (30 mL) under argon at room temperature was treated succesively with 4-fluoroaniline (1.80 g, 0.016 mol), sodium triacetoxyborohydride (5.12 g, 0.024 mol) and acetic acid (1 mL). After stirring for two hours, the mixture was concentrated, dissolved in ethyl acetate and washed 5% sodium bicarbonate, water and brine. The dried (anhydrous magnesium sulfate) organic solution was concentrated and crystallized from ether/hexanes to give the title product (2.07 g, 65%) as a colorless solid, mp 72°-73° C. Analysis calculated for C10H12 FNO2 ·0.07 H2O: C, 60.54; H, 6.16; N, 7.06; F, 9.58. Found: C, 60.75; H, 6.15; N, 6.96; F, 9.13. the mixture was concentrated dissolved in ethyl acetate washed 5% sodium bicarbonate, water and brine The dried (anhydrous magnesium sulfate) organic solution was concentrated crystallized from ether/hexanes