Ethyl S-4-chloro-3-hydroxybutyrate
- CAS NO.:86728-85-0
- Empirical Formula: C6H11ClO3
- Molecular Weight: 166.6
- MDL number: MFCD00211241
- EINECS: 617-912-5
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-08-21 22:41:43
What is Ethyl S-4-chloro-3-hydroxybutyrate?
Chemical properties
Colorless to light yellow liqui
The Uses of Ethyl S-4-chloro-3-hydroxybutyrate
Atorvastatin Intermediate
The Uses of Ethyl S-4-chloro-3-hydroxybutyrate
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.
What are the applications of Application
Ethyl (S)-(?)-4-chloro-3-hydroxybutyrate is an alkyl halide and potentially useful chiral synthetic reagent
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.
Properties of Ethyl S-4-chloro-3-hydroxybutyrate
Boiling point: | 93-95 °C5 mm Hg(lit.) |
alpha | -14.5 º (c=neat) |
Density | 1.19 g/mL at 25 °C(lit.) |
refractive index | n |
Flash point: | 109 °C |
storage temp. | Keep in dark place,Sealed in dry,Room Temperature |
form | Liquid |
pka | 13.23±0.20(Predicted) |
color | Clear colorless to yellow |
optical activity | [α]23/D 14°, neat |
BRN | 4657170 |
InChI | InChI=1S/C6H11ClO3/c1-2-10-6(9)3-5(8)4-7/h5,8H,2-4H2,1H3/t5-/m0/s1 |
CAS DataBase Reference | 86728-85-0(CAS DataBase Reference) |
Safety information for Ethyl S-4-chloro-3-hydroxybutyrate
Signal word | Danger |
Pictogram(s) |
Corrosion Corrosives GHS05 Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H318:Serious eye damage/eye irritation |
Precautionary Statement Codes |
P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Ethyl S-4-chloro-3-hydroxybutyrate
InChIKey | ZAJNMXDBJKCCAT-YFKPBYRVSA-N |
SMILES | C(OCC)(=O)C[C@H](O)CCl |
Abamectin manufacturer
TEADUS PHARMA PRIVATE LIMITED
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