(S)-4-Chloro-3-hydroxybutyronitrile Chemical Properties

Boiling point:

110 °C/1 mmHg(lit.)

Density 

1.250 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.474(lit.)

Flash point:

110 °C

storage temp. 

2-8°C

solubility 

Chloroform (Sparingly), Methanol (Slightly)

pka

12.67±0.20(Predicted)

form 

Oil

color 

Clear Colourless

optical activity

Consistent with structure

InChI

InChI=1S/C4H6ClNO/c5-3-4(7)1-2-6/h4,7H,1,3H2/t4-/m0/s1

InChIKey

LHBPNZDUNCZWFL-BYPYZUCNSA-N

SMILES

C(#N)C[C@H](O)CCl

CAS DataBase Reference

127913-44-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

HS Code 

29269090

MSDS

• Language:English Provider:(S)-4-Chloro-3-hydroxybutyronitrile

(S)-4-Chloro-3-hydroxybutyronitrile Usage And Synthesis

Chemical Properties

Colorless to light yellow liqui

Uses

(3S)-4-Chloro-3-hydroxybutyronitrile is used in various organic precursor syntheses. It is used in the synthesis of hydroxypyrrolidinones to by used as carbapenem precursors. Also used in the preparation of atorvastatin (A791750) precursors. Impurity in the synthesis of Rosuvastatin (R700500), a selective, competitive HMG-CoA reductase inhibitor. Antilipemic.

Synthesis

1. 75 L of water was added to the reactor followed by (S)-epichlorohydrin (99.3% ee). Under stirring conditions, 4.76 kg of 25% aqueous sodium cyanide and 3.30 kg of 50% aqueous citric acid were slowly added dropwise for 1 h. 2. The pH was maintained between 7.9 and 8 during the reaction, and the temperature was controlled at 22-25°C for 50 min. 3. After completion of the reaction, stirring was continued for 10 h. Then 0.7 kg of sodium chloride was added and stirred until it was The reaction mixture was extracted with 20 L of ethyl acetate and the organic layer was separated. 5. 0.2 kg of anhydrous sodium sulfate was added to the ethyl acetate layer, stirred for 30 min and filtered. 6. The ethyl acetate was removed by evaporation under reduced pressure, and the residue was distilled through a membrane distiller at 110°C/1 mbar to give 1.77 kg of (S)-4-chloro-3-hydroxybutanenitrile (Yield 91.3%, chemical purity 99.1%). 7. and 99.1% chemical purity).7. The optical purity of the product was determined to be 99.3% ee by GC analysis.8. The experiments were repeated under different reaction conditions according to the same method and the results are summarized in Table 1.

References

[1] Synthesis, 2004, # 16, p. 2629 - 2632
[2] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 9-10
[3] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 10
[4] Patent: WO2005/87715, 2005, A1. Location in patent: Page/Page column 10

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