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

HRID 1892068Notes

Reaction equation

HRID 1892068 reaction equation
[H][H].[C:3]([NH:6][C:7](=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:5])[CH3:4]>CO>[C:3]([NH:6][C@H:7]([C:8]([OH:10])=[O:9])[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)(=[O:5])[CH3:4]

Participants

4

Reactant 2

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

Product 1

HCID 74839N-Acetyl-L-phenylalanine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The organic inorganic composite material 2-13 (50 mg) and 2 mg (4.9 mmol) of bis(cyclooctadiene)rhodium (I) tetrafluoroborate were stirred in 3 ml of methanol at room temperature for 30 minutes in a hydrogen atmosphere of 1 atm. 105 mg (0.51 mmol) of α-(acetoamido)cinnamic acid was added to the resulting mixture, and reaction was conducted at room temperature for 30 minutes. Thus, N-acetyl-phenylalanine was obtained. An enantiomer excess of D-form determined by HPLC analysis (Chirace AD-H, manufactured by Daicel) was 97% e.e.

Sources & evidence

ORD record
ord-85397887f5b542ffa972927153c546c4
Source dataset
uspto-grants-2013_08
Patent number
US08507630B2

Reaction notes

Loading…