反应详情

温度

0 °C

1,4-Dioxane (20 ml) is added to a solution of guanidine hydrochloride (0.96 g, 10 mmol) and sodium hydroxide (0.8 g, 20 mmol) in water (10 ml) and the resulting mixture is cooled to 0° C. Benzyloxycarbonyl chloride (1.1 ml, 7.7 mmol) is added dropwise with vigorous stirring over a period of 10 min. After the addition is completed, the ice-bath is removed and stirring is continued for 1 h at room temperature. The mixture is concentrated in vacuo to one third of its original volume and extracted three times with ethyl acetate (20 ml each). The combined extracts are washed with brine (20 ml) and dried with anhydrous sodium sulfate. After filtering and removal of the solvent under reduced pressure N-Cbz-guanidine (1.31 g, 88%) is obtained as a white powder: mp: 120-122° C.; 1H NMR (360 MHz, DMSO-d6) δ 7.35-7.25 (m, 5H), 6.88 (br s, 4H), 4.95 (s, 2H); Electrospray-MS m/e 194 (M+H+).

1. additionAfter the addition
2. customthe ice-bath is removed
3. stirringstirring
4. waitis continued for 1 h at room temperature
5. concentrationThe mixture is concentrated in vacuo to one third of its original volume
6. extractionextracted three times with ethyl acetate (20 ml each)
7. washThe combined extracts are washed with brine (20 ml)
8. dry with materialdried with anhydrous sodium sulfate
9. filtrationAfter filtering
10. customremoval of the solvent under reduced pressure N-Cbz-guanidine (1.31 g, 88%)
11. customis obtained as a white powder