Sodium Hydroxide → rac-(1R,2S)-2-(methoxycarbonyl)cyclohexane-1-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

Into a 100 mL jacketed vessel was placed dimethyl cyclohexane-1,2-dicarboxylate (2, 4 g, 20 mmol) and 39 mL of 0.1M potassium phosphate buffer, pH 8. The mixture was continuously stirred at 40° C. and Novozym™ 435 (320 mg) was added. Stirring was continued at 40° C. for 43 hours and pH was maintained at 8 by addition of 2M NaOH solution. A sample from the reaction was analyzed by GC to confirm that less than 5% of the starting material remained. The reaction mixture was filtered to remove the enzyme and the filtrate was extracted with toluene (20 mL) to remove any residual starting material. The pH of the aqueous phase was readjusted to 3.5 with 2M HCl and it was extracted with 2×50 mL of MTBE. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure to yield 3.2 g (86%) of (1S,2R)-2-(methoxycarbonyl) cyclohexane carboxylic acid (3) as a colorless oil with e.e.=98%. The isolated enzyme is washed with fresh buffer for reuse with a second batch of substrate/buffer.

Provenance & Evidence