Réaction #1121747

Équation de réaction

5-methyl-3-nitromethyl-hexanoic acid ethyl ester

NaOH

→

(S)-5-methyl-3-nitromethyl-hexanoic acid ethyl ester

Rendement 43.0%

Conditions de réaction

Traitement

1. 1
   AutreAfter 55% conversion (corresponds to 50.6 mL of NaOH consumption) the reaction
2. 2
   workup.ADDITIONwas stopped by addition of 100 mL of ethyl acetate
3. 3
   workup.ADDITION100 mL of 5M aqueous NaOH were added
4. 4
   Autrethe layers were separated
5. 5
   LavageThe aqueous layer was washed once with 100 mL of ethyl acetate
6. 6
   ConcentrationThe combined organic layers were concentrated under reduced pressure

Mode opératoire

100 g of 5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl) were added to an aqueous solution of EstB (500 mL cell extract; ˜5 g total protein concentration). At a temperature of 25° C. the pH was kept at 7.0 by continuous addition of 5M aqueous NaOH. After 55% conversion (corresponds to 50.6 mL of NaOH consumption) the reaction was stopped by addition of 100 mL of ethyl acetate. 100 mL of 5M aqueous NaOH were added and the layers were separated. The aqueous layer was washed once with 100 mL of ethyl acetate. The combined organic layers were concentrated under reduced pressure to give 43 g of (S)-5-methyl-3-nitromethyl-hexanoic acid ethyl ester (VIII, R1=ethyl; ee=98%).

Source