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HomeProduct name listEthyl S-4-chloro-3-hydroxybutyrate

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
Ethyl S-4-chloro-3-hydroxybutyrate Structural

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  n20/D 1.453(lit.)
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)
ghs
Corrosion
Corrosives
GHS05
ghs
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

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