HCID 18987060, compound → HCID 53965125, compound

HRID 2396425Notes

Reaction equation

HRID 2396425 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 38.3%

Reagents, catalysts & solvents 1

HCID 24243Trisodium PhosphateSolvent

Procedure

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.

Workup

  1. additionis added crude Candida
  2. additionThe reaction is treated with a Celite filtration
  3. extractionextracted with 2×25 mL ethyl acetate
  4. additionThe combined extracts are treated with brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f7da0c9355e49319400ad0c15cd3813
Source dataset
uspto-grants-1996_02
Patent number
US05492830

Reaction notes

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