Methyl alpha-acetamidocinnamate → Acetylphenylalanine methyl ester

HRID 1906707

Reaction equation

HRID 1906707 reaction equation
[C:1]([NH:4][C:5](=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7])(=[O:3])[CH3:2]>C(OCC)(=O)C>[CH3:9][O:8][C:6](=[O:7])[C@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[NH:4][C:1](=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 340163Methyl alpha-acetamidocinnamate

Product 1

HCID 704002Acetylphenylalanine methyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A second recycling of the catalyst is performed under the conditions described above, but introducing methyl α-acetamidocinnamate (1.6 g) and ethyl acetate (10 cc). Pure N-acetylphenylalanine methyl ester (1.33 g) is thus obtained with a conversion of 100%, its rotatory power being:

Sources & evidence

ORD record
ord-e343201433b347ff99acb0176de1801c
Source dataset
uspto-grants-1987_03
Patent number
US04654176

Linked notes

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