methyl 2-amino-2-(2-iodophenyl)acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-iodobenzoic acid (6.4 g, 25.8 mmol) in THF (90 mL) is added HOBt (3.5 g, 25.8 mmol). After the mixture is stirred at RT for 10 min, EDCl (4.93 g, 25.8 mmol) is added followed by triethylamine (4.9 mL, 34.4 mmol). The mixture is stirred at RT for 40 min then amino-(2-iodophenyl)-acetic acid methyl ester (5.0 g, 17.2 mmol) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-60% EtOAc/hexane as eluent to give the title compound. The mixture is stirred at RT for 40 min stirring is continued for 18 h The solvent is removed under reduced pressure and water is added to the residue The mixture is extracted with EtOAc the organic phase is washed with brine dried over magnesium sulfate The solvent is removed under reduced pressure the residue purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of azido-(2-iodophenyl)-acetic acid methyl ester in THF (100 mL) is added triphenylphosphine (28.5 g, 109 mmol) in portions. The mixture is stirred at RT for 2 h then water (4 mL) is added and is heated to reflux. The solvent is removed under reduced pressure and ether (50 mL) is added followed by 2N HCl until acidic. The aqueous phase is washed with methylene chloride then is concentrated and basified with NaOH/ice until pH 12. The mixture is extracted with methylene chloride (3×200 mL) and the combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound. is heated to reflux The solvent is removed under reduced pressure and ether (50 mL) is added The aqueous phase is washed with methylene chloride then is concentrated The mixture is extracted with methylene chloride (3×200 mL) the combined organic phases are dried over sodium sulfate The solvent is removed under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-iodobenzoic acid (6.4 g, 25.8 mmol) in THF (90 mL) is added HOBt (3.5 g, 25.8 mmol). After the mixture is stirred at RT for 10 min, EDCl (4.93 g, 25.8 mmol) is added followed by triethylamine (4.9 mL, 34.4 mmol). The mixture is stirred at RT for 40 min then amino-(2-iodophenyl)-acetic acid methyl ester (5.0 g, 17.2 mmol) is added and stirring is continued for 18 h. The solvent is removed under reduced pressure and water is added to the residue. The mixture is extracted with EtOAc and the organic phase is washed with brine and dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue purified by flash chromatography using a gradient of 0-60% EtOAc/hexane as eluent to give the title compound. The mixture is stirred at RT for 40 min stirring is continued for 18 h The solvent is removed under reduced pressure and water is added to the residue The mixture is extracted with EtOAc the organic phase is washed with brine dried over magnesium sulfate The solvent is removed under reduced pressure the residue purified by flash chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of azido-(2-iodophenyl)-acetic acid methyl ester in THF (100 mL) is added triphenylphosphine (28.5 g, 109 mmol) in portions. The mixture is stirred at RT for 2 h then water (4 mL) is added and is heated to reflux. The solvent is removed under reduced pressure and ether (50 mL) is added followed by 2N HCl until acidic. The aqueous phase is washed with methylene chloride then is concentrated and basified with NaOH/ice until pH 12. The mixture is extracted with methylene chloride (3×200 mL) and the combined organic phases are dried over sodium sulfate. The solvent is removed under reduced pressure to give the title compound. is heated to reflux The solvent is removed under reduced pressure and ether (50 mL) is added The aqueous phase is washed with methylene chloride then is concentrated The mixture is extracted with methylene chloride (3×200 mL) the combined organic phases are dried over sodium sulfate The solvent is removed under reduced pressure