反应详情

温度

0 °C

The title compound was prepared by a modification of the procedure by Heimer et al. (Int. J. Pept., 1984, 23, 203-211). N-(2-Aminoethyl)glycine (1, 3 g, 25.4 mmol) was dissolved in water (50 mL), dioxane (50 mL) was added, and the pH was adjusted to 11.2 with 2 N sodium hydroxide. tert-Butyl-4-nitrophenyl carbonate (7.29 g, 30.5 mmol) was dissolved in dioxane (40 mL) and added dropwise over a period of 2 h, during which time the pH was maintained at 11.2 with 2 N sodium hydroxide. The pH was adjusted periodically to 11.2 for three more hours and then the solution was allowed to stand overnight. The solution was cooled to 0° C. and the pH was carefully adjusted to 3.5 with 0.5 M hydrochloric acid. The aqueous solution was washed with chloroform (3×200 mL), the pH adjusted to 9.5 with 2N sodium hydroxide and the solution was evaporated to dryness, in vacuo (14 mm Hg). The residue was extracted with DMF (25+2×10 mL) and the extracts filtered to remove excess salt. This results in a solution of the title compound in about 60% yield and greater than 95% purity by tlc (system 1 and visualised with ninhydrin, Rf=0.3). The solution was used in the following preparations of BOC-aeg derivates without further purification.

1. customThe title compound was prepared by a modification of the procedure by Heimer et al. (Int. J. Pept., 1984, 23, 203-211)
2. additionadded dropwise over a period of 2 h, during which time the pH
3. washThe aqueous solution was washed with chloroform (3×200 mL)
4. customthe solution was evaporated to dryness, in vacuo (14 mm Hg)
5. extractionThe residue was extracted with DMF (25+2×10 mL)
6. filtrationthe extracts filtered
7. customto remove excess salt