Ethyl S-4-chloro-3-hydroxybutyrate Chemical Properties

alpha 

-14.5 º (c=neat)

Boiling point:

93-95 °C5 mm Hg(lit.)

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

InChIKey

ZAJNMXDBJKCCAT-YFKPBYRVSA-N

SMILES

C(OCC)(=O)C[C@H](O)CCl

CAS DataBase Reference

86728-85-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

41-22

Safety Statements 

26-36-39

RIDADR 

2810

WGK Germany 

3

HazardClass 

6.1

PackingGroup 

III

HS Code 

29181990

MSDS

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Ethyl S-4-chloro-3-hydroxybutyrate Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

Atorvastatin Intermediate

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.

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.

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