Water → 63060-94-6

HRID 1097174Notes

Reaction equation

HRID 1097174 reaction equation
COC(C)(C)C.O.[NH2:8][CH:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11].[ClH:22].C(O)C>C1CCCCC1>[ClH:22].[NH2:8][C@H:9]([CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 15413tert-Butyl methyl etherHCID 102688Ethyl 3-phenyl-DL-alaninateHCID 21887872Ethanol hydrochloride

Product 1

HCID 1300100163060-94-6

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Conditions

Temperature
30 °C

Procedure

To 80 mL of t-butyl methyl ether saturated with water were added 4.00 g (20.7 mmol) of ethyl 2-amino-3-phenylpropionate (racemic mixture) and 800 mg of a lipase (AMANO LIPASE PS (Trade name); available from ALDRICH CORPORATION) originated from Burkholderia cepacia (Pseudomonas cepacia), and the mixture was reacted with stirring at 30° C. After 168 hours, the reaction mixture was filtered, dried over magnesium sulfate, filtered, concentrated under reduced pressure and 12 mL of cyclohexane was added to the residue. To the resulting cyclohexane solution was added 1.52 g (10.1 mmol of hydrochloric acid) of a hydrochloric acid-ethanol solution (hydrochloric acid content: 24.3% by weight) at 0° C. and the mixture was stirred at the same temperature for 1 hour. The reaction mixture was filtered to obtain 1.90 g (Yield based on ethyl 2-amino-3-phenylpropionate (racemic mixture)=40.0%) of ethyl (R)-2-amino-3-phenylpropionate hydrochloride as white crystals.

Workup

  1. customthe mixture was reacted
  2. filtrationthe reaction mixture was filtered
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure and 12 mL of cyclohexane
  6. additionwas added to the residue
  7. stirringthe mixture was stirred at the same temperature for 1 hour
  8. filtrationThe reaction mixture was filtered
  9. customto obtain 1.90 g (Yield based on ethyl 2-amino-3-phenylpropionate (racemic mixture)=40.0%) of ethyl (R)-2-amino-3-phenylpropionate hydrochloride as white crystals

Sources & evidence

ORD record
ord-9c1b6aee1ed14704874f44fde78e05f1
Source dataset
uspto-grants-2012_03
Patent number
US08143052B2

Reaction notes

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