2-Naphthoyl chloride → 3-cyano-N-(2-naphthoyl)-L-alanine
Reaction equation
[C:1]([CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5])#[N:2].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19](Cl)=[O:20]>[OH-].[Na+]>[C:1]([CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH:5][C:19]([C:10]1[CH:11]=[CH:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=1)=[O:20])#[N:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
0.114 g of 3-cyano-L-alanine was dissolved in 5 ml of 1N sodium hydroxide solution and treated with 0.285 g of 2-naphthoyl chloride at 0° C. After acidification with 2M hydrochloric acid and flash chromatography on silica gel using 25% methanol in dichloromethane for the elution there was obtained 0.049 g of 3-cyano-N-(2-naphthoyl)-L-alanine of melting point 95°-100° C.