Chemical Properties
Colorless to light yellow liqui
Uses
Ethyl (
S)-(?)-4-chloro-3-hydroxybutyrate can be used as a starting material in the synthesis of 4-amino-3-hydroxybutyric acid, a compound of pharmacological importance.
Uses
Atorvastatin Intermediate
Biosynthesis
Bioreductions catalyzed by alcohol dehydrogenases (ADHs) play an essential role in synthesizing chiral alcohols. A novel ADH, SmADH31, obtained from the Stenotrophomonas maltophilia genome, which can tolerate extremely high concentrations (6 M) of both substrate and product. The coexpression of SmADH31 and glucose dehydrogenase from Bacillus subtilis in Escherichia coli meant that as much as 660 g L–1 (4.0 M) ethyl 4-chloroacetoacetate was completely converted into ethyl (S)-4-chloro-3-hydroxybutyrate [(S)-CHBE] in a monophasic aqueous system with a >99.9% ee value and a high space-time yield (2664 g L–1 d–1). In the 100 ml-scale monophasic aqueous system (in triplicate), 66.0 g COBE (single batch charge) can be completely converted to (S)-CHBE (ee >99.9%) in only 6 h with 2 g of the SmADH31/GDH co-expressing cells. After extraction and evaporation, 61.6 g (S)-CHBE was isolated with 92% yield[1].
General Description
Ethyl (
S)-4-chloro-3-hydroxybutanoate is a chiral intermediate generally used to prepare atorvastatin, a cholesterol-lowering drug.
References
[1] Zeyu Yang. “Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System.” Organic Process Research & Development 24 6 (2020): 1068–1076.
