ChemicalBook CAS DataBase List (R)-(-)-3-HYDROXYBUTYRONITRILE

(R)-(-)-3-HYDROXYBUTYRONITRILE synthesis

14synthesis methods

Product Name:(R)-(-)-3-HYDROXYBUTYRONITRILE
CAS Number:125103-95-9
Molecular formula:C4H7NO
Molecular Weight:85.1

4368-06-3 Synthesis

4368-06-3
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$150.00/1g

6168-83-8
100 suppliers
$30.00/25 mg

625-72-9 Synthesis

625-72-9
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$36.00/100mg

123689-95-2 Synthesis

123689-95-2
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125103-95-9
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Yield: 13.9 % ee ， 31.6 % ee

Reaction Conditions:

with bacterial isolate in aq. phosphate buffer; pH=7.2 at 15;

Steps:

2.9 _{RRN 27,28}General procedure for large scale biotransformation towards 3-hydroxybutyronitrile
General procedure: The procedure for large scale biotransformation of racemic 3-hydroxybutyronitrile was similar to the general procedure, with the exception of the use of potassium phosphate buffer (0.1 M, pH 7.0, 100 mL) containing 3-hydroxybutyronitrile (85.1 mg, 10 mM). The resulting aqueous solution was basified to pH 12 with aqueous NaOH (2 M) and extracted with ethyl acetate (3 × 100 mL). The aqueous solution was acidified using aqueous HCl (2 M) to pH 2 and extracted with ethyl acetate (3 × 100 mL), dried over MgSO₄ and the solvent removed under vacuum. The crude product was subjected to silica gel column chromatography eluted with a mixture of hexane and ethyl acetate (1:1) to give 3-hydroxybutyric acid in 42% yield (44 mg, 4.23 mmol) as clear oil. The configuration of the corresponding acid was determined by comparing the direction of specific rotation with that of an authentic sample. Enantiomeric excess values were obtained from HPLC analysis using a column of chiral stationary phase and correlated with literature. (R)-enantiomer elutes at 11.94 min, (S)-enantiomer elutes at 12.34 min [34]. ¹H NMR (400 MHz, CDCl₃) δ = 4.19-4.27 (1H, m), δ = 2.45-2.58 (2H, m), δ = 1.23 (3H, d, J = 6.3 Hz). ¹³C NMR (400 MHz, CDCl₃) δ = 117, 76, 64, 42, 22 [α]^d₂₅ = +4.0 (c = 2.5, MeOH), and compared with that in the literature [α]^d₂₅ = +4.1 (c = 2.7, MeOH) [35]. This experiment was performed in triplicate.

References:

Coady, Tracey M.;Coffey, Lee V.;O'Reilly, Catherine;Owens, Erica B.;Lennon, Claire M. [Journal of Molecular Catalysis B: Enzymatic,2013,vol. 97,p. 150 - 155]