Reaction #1914828

Reaction equation

water

calcium acetate

2-methyglutaronitrile

water

N-methylpropionamide

water

→

2-methylglutaric acid diammonium salt

4-cyanopentanoic acid ammonium salt

2-methylglutaronitrile

Solvents

HCl

Conditions

Workup

1. 1
   Otherreaction vessel (temperature-controlled at 30° C. with a recirculating temperature bath)
2. 2
   FiltrationThe resulting mixture was filtered (0.22 μm)
3. 3
   workup.WAITthe reaction was complete in less than 2.5 h

Procedure

Into a 125 mL jacketed reaction vessel (temperature-controlled at 30° C. with a recirculating temperature bath) was placed 16.5 g of E. coli SW91/alginate beads prepared as described in Example 10. To the reaction vessel was added 68.25 mL of water, 1.0 mL of 0.20 M calcium acetate buffer (pH 7.0), and 14.25 mL (13.54 g, 1.25 M) of 2-methyglutaronitrile, and the mixture stirred at 30° C. Samples (0.100 mL) were mixed with 0.400 mL of water, then 0.360 mL of the diluted sample was mixed with 0.040 mL of 0.75 M N-methylpropionamide in water and 0.020 mL of 6.0 N HCl. The resulting mixture was filtered (0.22 μm) and the filtrate analyzed by HPLC for 2-methylgluratonitrile, 4-cyanopentanoic acid and 2-methlglutaric acid. The rate of production of 4-cyanopentanoic acid was 739 mM/h, and the reaction was complete in less than 2.5 h. At complete conversion of 2-methylglutaronitrile, the yields of 4-cyanopentanoic acid ammonium salt and 2-methylglutaric acid diammonium salt were 98.5% and 1.5% yields, respectively.

Source