反应详情

Acetylthiopropionic acid (0.5 g, 3.38×10−3 mol, see Example 2), methylamine hydrochloride (0.25 g, 3.7×10−3 mol) and pyridine (0.58 ml, 7.2×10−3 mol) were dissolved in 15 ml anhydrous dimethylformamide. The reaction was started by addition of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.71 g, 3.7×10−3 mol). The reaction was stirred over argon at room temperature for 5 hr. The solvents were removed in vacuo to afford a yellow oil. After addition of 5 ml water and 1 ml 0.5 M potassium phosphate, pH 7, to the oil, the pH of the solution was carefully adjusted to 7.0 with 10 N KOH. The aqueous solution was extracted 4 times, each with 25 ml methylene chloride. The organic phase was dried with anhydrous magnesium sulfate and filtered. The solvents were removed in vacuo, 10 ml ethyl alcohol was added to the residue, and the solvent was removed in vacuo to remove traces of pyridine. Ethyl acetate (1.5 ml) was added to the crystalline residue and the slight precipitate was filtered. The solvent was removed in vacuo and the compound was dried overnight in a vacuum desiccator. 0.43 g of the desired compound was recovered which melted at 67-70° C.

1. customThe solvents were removed in vacuo
2. customto afford a yellow oil
3. extractionThe aqueous solution was extracted 4 times
4. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
5. filtrationfiltered
6. customThe solvents were removed in vacuo, 10 ml ethyl alcohol
7. additionwas added to the residue
8. customthe solvent was removed in vacuo
9. customto remove traces of pyridine
10. additionEthyl acetate (1.5 ml) was added to the crystalline residue
11. filtrationthe slight precipitate was filtered
12. customThe solvent was removed in vacuo
13. customthe compound was dried overnight in a vacuum desiccator
14. custom0.43 g of the desired compound was recovered which melted at 67-70° C.