HCID 18987060, compound → HCID 53965125, compound

Participants

Reaction Steps

To a suspension of ethyl (±)-2-hydroxy-2-methyl-3-(3,4-dimethoxyphenyl)propionate (301.1 mg, 1.12 mmol) in 50 mL of 50 mM sodium phosphate buffer pH 7.5 is added carboxypeptidase Y from Bakers Yeast (7.6 mg of protein). After 23 h, 90.6% conversion is observed by HPLC (C18 column, 254 nm detection, acid tR =5.8 min and ester tR =11.6 min). The reaction is 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 (36.2 mg, 0.135 mmol, 12.1%). 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 31.2% (R -enantiomer.

Provenance & Evidence