2-(Acetylamino)-3-phenyl-2-propenoic acid → (-)-N-Acetylphenylalanine

HRID 1585234Notes

Reaction equation

HRID 1585234 reaction equation
[C:1]([NH:4][C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]>CO>[C:1]([NH:4][C@@H:5]([C:6]([OH:8])=[O:7])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 956312-(Acetylamino)-3-phenyl-2-propenoic acid

Product 1

HCID 101184(-)-N-AcetylphenylalanineYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of α-acetamido-cinnamic acid (0.5 g, 2.44 mmol) and the catalyst (1) (16 mg, 0.024 mmol, 1.0 mol %) in degassed methanol (10 ml) was placed in a 50 ml Parr pressure reactor purged with nitrogen. The vessel was then purged with hydrogen (×3) and charged to 4.34 MPa (630 psi) of hydrogen. After stirring for 2 h, the solution was evaporated to give (R)-N-acetylphenylalanine (0.52 g, quantitative yield, 84.4% ee).

Workup

  1. custompurged with nitrogen
  2. customThe vessel was then purged with hydrogen (×3)
  3. additioncharged to 4.34 MPa (630 psi) of hydrogen
  4. customthe solution was evaporated

Sources & evidence

ORD record
ord-fa106a2640c349d69c0abce0fd5a76e8
Source dataset
uspto-grants-1999_08
Patent number
US05936109

Reaction notes

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