Ethanol → ethyl (2R)-2-amino-3-phenylpropanoate

HRID 1612397Notes

Reaction equation

HRID 1612397 reaction equation
[NH2:1][C@@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:13][CH2:14]O>>[CH2:13]([O:11][C:10](=[O:12])[C@@H:2]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[NH2:1])[CH3:14]

Participants

3

Reactant 2

HCID 702EthanolHCID 71567D-Phenylalanine

Product 1

HCID 721861ethyl (2R)-2-amino-3-phenylpropanoateYield 81%

Procedure

D-Phenylalanine (250 mg, 1.52 mmol) was dissolved in 5 ml EtOH previously bubbled in HCl (gas). The solution was brought to 100° C. and allowed to reflux overnight. The solvent was evaporated off affording 280 mg crude product. Recrystallization from EtOH/EtOAc/pentane gave 239 mg (81% yield) of D-phenylalanine ethyl ester as white crystals.

Workup

  1. custompreviously bubbled in HCl (gas)
  2. customwas brought to 100° C.
  3. temperatureto reflux overnight
  4. customThe solvent was evaporated off
  5. customaffording 280 mg crude product
  6. customRecrystallization from EtOH/EtOAc/pentane

Sources & evidence

ORD record
ord-81a151e82ee74a4a8054a3950ed94f7e
Source dataset
uspto-grants-2006_01
Patent number
US06992207B2

Reaction notes

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