2-(Acetylamino)-3-phenyl-2-propenoic acid → N-Acetyl-L-phenylalanine

HRID 1065155Notes

Reaction equation

HRID 1065155 reaction equation
[NH:1]([C:5](=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]([OH:8])=[O:7])[C:2]([CH3:4])=[O:3].[H][H]>C(O)C>[C:2]([NH:1][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])[CH3:4]

Participants

4

Reactant 2

HCID 956312-(Acetylamino)-3-phenyl-2-propenoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 74839N-Acetyl-L-phenylalanineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With the catalyst prepared as in example 7 there have been reduced 0.725 g of 3-acetoxy, 4-methoxy, alpha-acetaminocinnamic acid dissolved in 25 mls of anhydrous ethanol. The reaction has been carried out in an autoclave (glass) with a hydrogen pressure of 2 atm at room temperature. There has been obtained 3-acetoxy, 4-methoxy, N-acetylphenylalanine with an optical yield of 58%. [α]D22 =+12.8 (c=1, acetone) the [α]D22 (c=1, acetone) of enantiomerically pure 3-acetoxy, 4-methoxy N-acetylphenylalanine=22.

Workup

  1. customWith the catalyst prepared as in example 7 there

Sources & evidence

ORD record
ord-ef53532078424f39867986e4a97ebf8a
Source dataset
uspto-grants-1982_05
Patent number
US04328364

Reaction notes

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