Novozyme 435-catalyzed asymmetric acylation of (R, S)-3-n- butylphthalide in hexane.
The asymmetric acylation of (R, S)-3-n-butylphthalide could be efficiently catalyzed by Novozyme 435. The effect of various reaction parameters such as water activity, temperature, molar ratio of acetic anhydride to (R, S)-3-n-butylphthalide, and reaction time on the asymmetric acylation were studied. The optimums of the reaction parameters were water activity 0.62, temperature 30 degrees C, molar ratio of acetic anhydride to (R, S)-3-n-butylphthalide 8:1, and reaction time 48 h, respectively. Under the optimum conditions, enantiopure 3-n-butylphthalide with an optical purity of 95.7% enantiomeric excess and 49.1% yield could be obtained. Furthermore, the enantiomeric excess of product was over 98%.
School of Chemical Engineering, Guizhou University, Caijiaguan, Guiyang, Guizhou Province, PR China. helaping998@gmail.com
Laping
L
He
Cuiqin
C
Li
Bing
B
Gao
D000215:Acylation; D001572:Benzofurans / Q000378:metabolism*; D002384:Catalysis; D002851:Chromatography, High Pressure Liquid; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D006586:Hexanes / Q000737:chemistry*; D007700:Kinetics; D008049:Lipase / Q000378:metabolism*; D013237:Stereoisomerism; D013696:Temperature
D001572:Benzofurans; D004800:Enzymes, Immobilized; D005656:Fungal Proteins; D006586:Hexanes; C027125:3-n-butylphthalide; C093667:Novozyme 435; D008049:Lipase