反应详情

2-(S)-[N-(tert-Butoxycarbonyl)amino]propanal was prepared from L-alanine according to the procedure described in the literature (Chakravarty et al, J. Med. Chem 1989, p1886). A mixture of the aldehyde (2.62 g), dimethylamine hydrochloride (2.47 g), sodium acetate (1.99 g) and sodium cyanoborohydride (1.43 g) in methanol (45 mL) was stirred at room temperature for 8 hours. The reaction mixture was dissolved in ethyl acetate, washed with water, dried (MgSO4), and the solvent removed in vacuo to yield a viscous oil. This was dissolved in dichloromethane, extracted with citric acid, basified with sodium hydroxide, and re-extracted with ethyl acetate. The organic layer was reduced in vacuo to yield the dimethylamino derivative as a white solid (586 mg).

1. washwashed with water
2. dry with materialdried (MgSO4)
3. customthe solvent removed in vacuo
4. customto yield a viscous oil
5. extractionextracted with citric acid
6. extractionre-extracted with ethyl acetate