Water → HCID 69218632, compound

HRID 269717Notes

Reaction equation

HRID 269717 reaction equation
O.[CH2:2]([NH:9][CH:10]([C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)[CH2:11][C:12]([O:14]C)=[O:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C>[CH2:2]([NH:9][C@H:10]([C:16]1[CH:21]=[CH:20][C:19]2[O:22][CH2:23][O:24][C:18]=2[CH:17]=1)[CH2:11][C:12]([OH:14])=[O:13])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium Bicarbonate2×HCID 23067187HCID 23067187, compound

Product 1

HCID 69218632HCID 69218632, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

To 4 mL of water were added 400 mg (1.28 mmol) of methyl (±)-3-benzylamino-3-(3,4-methylenedioxyphenyl)propionate and 107 mg (1.28 mmol) of sodium hydrogen carbonate, and the mixture was maintained to 30° C. To the resulting mixture was added 2 mg of lipase (CAL; available from Roche, CHIRAZYME L-2 (trade name)) originated from Candida antarctica at the same temperature, and the mixture was reacted at 30° C. while stirring. After 20 hours, at the time when the conversion rate of the starting materials reached 46.2%, 8 ml of ethyl acetate and 112 mg of sodium hydrogen carbonate were added to the reaction mixture and the aqueous layer was extracted. The resulting aqueous layer was adjusted to an inner pH of 2.0 with 2 mol/L of hydrochloric acid aqueous solution, and 8 ml of ethyl acetate and 500 mg of sodium chloride were added to the mixture to extract the organic layer. The resulting organic layer was dried over magnesium sulfate, filtered and concentrated to obtain 135 mg (Isolated yield based on methyl (±)-3-benzylamino-3-(4-fluorophenyl)propionate=35.3%) of (R) or (S)-3-benzylamino-3-(3,4-methylenedioxyphenyl)propionic acid as white crystal.

Workup

  1. additionTo the resulting mixture was added 2 mg of lipase (CAL; available from Roche, CHIRAZYME L-2 (trade name))
  2. customthe mixture was reacted at 30° C.
  3. additionwere added to the reaction mixture
  4. extractionthe aqueous layer was extracted
  5. additionwere added to the mixture
  6. extractionto extract the organic layer
  7. dry with materialThe resulting organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto obtain

Sources & evidence

ORD record
ord-e0bd93a5d5fd475292cb3774e9900941
Source dataset
uspto-grants-2008_11
Patent number
US07449325B2

Reaction notes

Loading…