HCID 18987060, compound → HCID 53965125, compound

HRID 2396426Notes

Reaction equation

HRID 2396426 reaction equation
[OH:1][C:2]([CH3:19])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>P([O-])([O-])([O-])=O.[Na+].[Na+].[Na+]>[OH:1][C@:2]([CH3:19])([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH3:18])[CH:10]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

3

Reactant 1

HCID 18987060HCID 18987060, compound

Product 1

HCID 53965125HCID 53965125, compoundYield 12.1%

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

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.

Workup

  1. additionis added carboxypeptidase Y from Bakers Yeast (7.6 mg of protein)
  2. extractionThe reaction is extracted with 2×25 mL ethyl acetate
  3. additionThe combined extracts are treated with brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6723dc4ce53844dda6c77f9e5de4b91f
Source dataset
uspto-grants-1996_02
Patent number
US05492830

Reaction notes

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