Reaction #40272

Reaction equation

2-isobutyl-succinonitrile

KOH

water

→

potassium (S)-3-cyano-5-methylhexanoate

Yield 31.3%

Conditions

Workup

1. 1
   Otherreaction vessels
2. 2
   Otherthe product mixtures were decanted
3. 3
   Otherleaving the enzyme catalyst
4. 4
   Otherin the reaction vessels
5. 5
   OtherReaction buffer (20 mL)
6. 6
   workup.ADDITIONwas added to the each reaction vessel
7. 7
   workup.STIRRINGstirred for approximately 2 min.
8. 8
   Otherdecanted
9. 9
   workup.ADDITIONadded to the product mixtures
10. 10
    workup.ADDITIONby adding
11. 11
    Other2-isobutyl-succinonitrile (6.81 g) and reaction buffer (118.2 mL) to each reaction vessel
12. 12
    workup.STIRRINGstirring the reaction
13. 13
    workup.WAITmixtures for 24 h
14. 14
    OtherAfter four reactions were completed in each vessel
15. 15
    Extractionextracted with MTBE (3×500 mL)
16. 16
    OtherThe MTBE extracts were removed
17. 17
    Extractionextracted with MTBE (2×500 mL)
18. 18
    ExtractionThe MTBE extract of the acidified aqueous part
19. 19
    Concentrationwas concentrated under vacuum
20. 20
    Otherto leave an oil, which
21. 21
    ConcentrationThe resulting solution was concentrated under vacuum

Procedure

Two 125 mL jacketed reaction vessels maintained at 30° C. were each charged with 2-isobutyl-succinonitrile (6.81 g), NIT-102 C2 (1.70 g) and 118.2 mL of reaction buffer. After stirring for 24 h, the product mixtures were decanted, leaving the enzyme catalyst in the reaction vessels. Reaction buffer (20 mL) was added to the each reaction vessel, stirred for approximately 2 min., and then decanted and added to the product mixtures. Reactions were repeated by adding 2-isobutyl-succinonitrile (6.81 g) and reaction buffer (118.2 mL) to each reaction vessel and stirring the reaction mixtures for 24 h. After four reactions were completed in each vessel (total of eight batch reactions), the product mixtures were combined and extracted with MTBE (3×500 mL). The MTBE extracts were removed and the aqueous part adjusted to pH 2.1 with phosphoric acid and extracted with MTBE (2×500 mL). The MTBE extract of the acidified aqueous part was concentrated under vacuum to leave an oil, which was treated with water (100 mL) and KOH (8.5 g). The resulting solution was concentrated under vacuum to give 24.2 g (31.3%) of potassium (S)-3-cyano-5-methylhexanoate. Methyl (S)-3-cyano-5-methylhexanoate was prepared from potassium (S)-3-cyano-5-methylhexanoate and analyzed by chiral GC to reveal an enantiomeric purity of 99.1% e.e.

Source