HCID 18987060, compound → HCID 53965125, compound

Participants

Reaction Steps

To a suspension of ethyl (±)-2-hydroxy-2-methyl-3-(3,4-dimethoxyphenyl)propionate (333.0 mg, 1.24 mmol) in 50 mL of 50 mM sodium phosphate buffer pH 7.5 is added crude Candida lipolytica ester hydrolase (22.6 mg of protein). After 24 h, 62% conversion is observed by HPLC (C18 column, 254 nm detection, acid tR =5.8 min and ester tR =11.6 min). The reaction is treated with a Celite filtration and then extracted with 2×25 mL ethyl acetate. The combined extracts are treated with brine, dried with magnesium sulfate, then concentrated in vacuo to yield ethyl (R)-2-hydroxy-2-methyl-3-(3,4-dimethoxyphenyl)propionate (127.4 mg, 0.475 mmol, 38.3%). The enantiomeric excess of the unreacted ester is determined by HPLC analysis (Chiracel OD column from J. T. Baker, 280 nm, (S)-enantiomer tR =6.6 min and (R)-enantiomer tR =8.3 min) to be 99% (R)-enantiomer.

Provenance & Evidence