benzyl 2-(phenylmethoxycarbonylamino)acetate

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

Procedure: To a mixture of 1.05 g. of N-benzyloxycarbonylglycine, 0.54 g. of benzylalcohol and 50 ml. of methylene chloride is added dropwise a solution of 1.31 g. of triphenyl phosphine and 1.10 g. of 2,2'-dipyridyl disulfide in 20 ml. of methylene chloride while stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for an additional 6 hours. The reaction mixture is treated with the same procedure as described above to give 1.36 g. of the desired product melting at 71° - 72°C. To a mixture of 1.05 g After completion of the addition The reaction mixture is treated with the same procedure to give 1.36 g

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

Procedure: A mixture of 2.09 g. of N-benzyloxycarbonylglycine, 2.62 g. of triphenyl phosphine, 2.61 g. of 2-nitrobenzenesulfenic acid benzyl ester, 2.20 g. of 2,2'-dipyridyl disulfide and 50 ml. of methylene chloride is stirred at room temperature for 3 hours. The reaction mixture is washed successively with water, saturated aqueous sodium bicarbonate, water, 0.1 N hydrochloric acid and water and then dried over anhydrous sodium sulfate. The solvent is distilled off. The residue is dissolved in methylene chloride. The solution is subjected to column chromatography using silica gel and eluted with methylene chloride. Distillation of the solvent from the eluate gives 2.51 g. of the desired product melting at 72°C. A mixture of 2.09 g The reaction mixture is washed successively with water, saturated aqueous sodium bicarbonate, water, 0.1 N hydrochloric acid and water dried over anhydrous sodium sulfate The solvent is distilled off The residue is dissolved in methylene chloride eluted with methylene chloride Distillation of the solvent from the eluate gives 2.51 g

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

Procedure: To a solution of N-benzyloxycarbonylglycine (0.42 g) and triethylamine (0.28 ml) in dioxane (5 ml), ethyl 2-benzyloxycarbonyloxyimino-2-cyanoacetate (0.55 g) is added, and the resulting mixture is stirred for 3 hours. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine benzyl ester (0.57 g) as an oil. The reaction mixture is treated as in Example A