D-对羟基苯甘氨酸甲酯

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In this preparation 1.81 g. of methyl α-amino-α-(4-hydroxyphenyl)acetate is dissolved in 10 ml. of dimethylformamide under nitrogen and 0.24 g. of sodium hydride is then added. The solution is stirred at room temperature under nitrogen until hydrogen evolution ceases and then 0.80 g. of chloromethyl methyl ether is added. The resulting mixture is warmed at 60° C for 1 hour and then cooled and diluted with water. The aqueous mixture is extracted with ether and the ether extract is dried and evaporated to afford methyl α-amino-α-(4-methoxymethoxyphenyl)acetate. In this preparation 1.81 g cooled The aqueous mixture is extracted with ether the ether extract is dried evaporated

实验步骤: 投料: 将原料溶于甲醇中无法溶清，加入氯化亚砜，溶液澄清，60℃加热回流搅拌1h原料反应完全； 旋干溶剂，得到2.63g白色固体，核磁鉴定结构正确。

实验步骤: 投料: 将原料溶于氨水中，室温下搅拌4h； LC-MS监测反应完全，旋干溶剂，得到0.13g白色固体； 核磁鉴定结构正确

实验步骤: 投料: 将原料溶于甲醇中，无法溶清，加入氯化亚砜溶液溶清，60℃加热回流，搅拌3h； LC-MS显示原料反应完全，但没有产品MS； 旋干溶剂，得到0.1g白色固体； 核磁确定结构，为目标产品；

实验步骤: 投料: 将原料溶于氨水中，室温搅拌2d（过周末）； LC-MS原料反应完全，但没有产品MS； 溶液析出固体，直接过滤（会有损失），拿到0.03g白色固体； 核磁推测为产品结构。

反应条件: temp:0.00; pressure:0.00; stir:

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

实验步骤: To a 0° solution of 2.50 g (11.48 mmol) of amino-(4-hydroxy-phenyl)-acetic acid methyl ester (from Example 178) in 125 mL of dichloromethane was added 10 mL of N,N-diisopropylethylamine followed by 2.97 g (11.48 mmol) of 9-fluorenylmethyl chlorformate and the resulting mixture was stirred at 0° for 2 h and room temperature for 2 h. The reaction mixture was then concentrated and the residue was diluted with ethyl acetate and water. The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide methyl(2R)-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}(4-hydroxyphenyl)ethanoate as a white solid. Electrospray Mass Spec 404.1 (M+H)+. The reaction mixture was then concentrated the residue was diluted with ethyl acetate and water The organics were washed with water dried over magnesium sulfate filtered concentrated in vacuo The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

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

实验步骤: To a 0° solution of 2.50 g (11.48 mmol) of amino-(4-hydroxy-phenyl)-acetic acid methyl ester (from Example 178) in 125 mL of dichloromethane was added 10 mL of N,N-diisopropylethylamine followed by 2.97 g (11.48 mmol) of 9-fluorenylmethyl chlorformate and the resulting mixture was stirred at 0° for 2 h and room temperature for 2 h. The reaction mixture was then concentrated and the residue was diluted with ethyl acetate and water. The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide methyl(2R)-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}(4-hydroxyphenyl)ethanoate as a white solid. Electrospray Mass Spec 404.1 (M+H)+. The reaction mixture was then concentrated the residue was diluted with ethyl acetate and water The organics were washed with water dried over magnesium sulfate filtered concentrated in vacuo The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

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

实验步骤: To 50 mL of methanol cooled to 0° C. was dropwise added 3.75 mL of thionyl chloride followed by 5.0 g (0.030 mmol) of D-4-hydroxyphenylglycine. The reaction was heated to reflux for 5 h then stirred overnight at room temperature. The resulting mixture was concentrated in vacuo and the residue was diluted with ether. The resulting solid was collected by filtration and dried in vacuo to provide 5.9 g of amino-(4-hydroxy-phenyl)-acetic acid methyl ester as a white solid. Electrospray Mass Spec 182.2 (M+H)+ The reaction was heated to reflux for 5 h The resulting mixture was concentrated in vacuo the residue was diluted with ether The resulting solid was collected by filtration dried in vacuo

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

实验步骤: To a 0° solution of 2.50 g (11.48 mmol) of amino-(4-hydroxy-phenyl)-acetic acid methyl ester (from Example 178) in 125 mL of dichloromethane was added 10 mL of N,N-diisopropylethylamine followed by 2.97 g (11.48 mmol) of 9-fluorenylmethyl chlorformate and the resulting mixture was stirred at 0° for 2 h and room temperature for 2 h. The reaction mixture was then concentrated and the residue was diluted with ethyl acetate and water. The organics were washed with water, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3) to provide methyl(2R)-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}(4-hydroxyphenyl)ethanoate as a white solid. Electrospray Mass Spec 404.1 (M+H)+. The reaction mixture was then concentrated the residue was diluted with ethyl acetate and water The organics were washed with water dried over magnesium sulfate filtered concentrated in vacuo The residue was chromatographed on silica gel eluting with ethyl acetate/hexanes (1:3)

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

实验步骤: To 50 mL of methanol cooled to 0° C. was dropwise added 3.75 mL of thionyl chloride followed by 5.0 g (0.030 mmol) of D-4-hydroxyphenylglycine. The reaction was heated to reflux for 5 h then stirred overnight at room temperature. The resulting mixture was concentrated in vacuo and the residue was diluted with ether. The resulting solid was collected by filtration and dried in vacuo to provide 5.9 g of amino-(4-hydroxy-phenyl)-acetic acid methyl ester as a white solid. Electrospray Mass Spec 182.2 (M+H)+. The reaction was heated to reflux for 5 h The resulting mixture was concentrated in vacuo the residue was diluted with ether The resulting solid was collected by filtration dried in vacuo