反応 #40272

反応方程式

2-isobutyl-succinonitrile

KOH

water

→

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

収率 31.3%

反応条件

後処理

1. 1
   その他reaction vessels
2. 2
   その他the product mixtures were decanted
3. 3
   その他leaving the enzyme catalyst
4. 4
   その他in the reaction vessels
5. 5
   その他Reaction buffer (20 mL)
6. 6
   workup.ADDITIONwas added to the each reaction vessel
7. 7
   workup.STIRRINGstirred for approximately 2 min.
8. 8
   その他decanted
9. 9
   workup.ADDITIONadded to the product mixtures
10. 10
    workup.ADDITIONby adding
11. 11
    その他2-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
    その他After four reactions were completed in each vessel
15. 15
    抽出extracted with MTBE (3×500 mL)
16. 16
    その他The MTBE extracts were removed
17. 17
    抽出extracted with MTBE (2×500 mL)
18. 18
    抽出The MTBE extract of the acidified aqueous part
19. 19
    濃縮was concentrated under vacuum
20. 20
    その他to leave an oil, which
21. 21
    濃縮The resulting solution was concentrated under vacuum

実験手順

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.

出典