Sodium Hydroxide → Sodium alpha-acetylaminocinnamate

HRID 65137

Reaction equation

HRID 65137 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:14])[C:5](=[CH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:6]=1.[OH-:15].[Na+:16]>O>[C:2]([NH:6][C:5](=[CH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:4]([O-:3])=[O:14])(=[O:15])[CH3:1].[Na+:16]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 949464-benzylidene-2-methyl-4H-oxazol-5-one2×

Product 1

HCID 70401301Sodium alpha-acetylaminocinnamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100-ml tightly-sealed glass vessel were charged 9.36 g of 2-methyl-4-benzylidene-5-oxazolone and 30 ml of water. Then, 5.3 g of 45% sodium hydroxide solution was added thereto and the resulting mixture was stirred at 40°-45° C. for two hours. The 2-methyl-4-benzylidene-5-oxazolone was hydrolyzed to form an aqueous homogeneous solution of sodium α-acetylaminocinnamate. The solution had a pH in excess of 12. 0.2 g of 5%-palladium-carbon was then added to the solution. After the gas phase in the vessel was purged with nitrogen and then with hydrogen, the reaction mixture in the vessel was subjected to catalytic reduction at 40°-45° C. under atmospheric pressure. The time required for the reduction was approximately four hours. After completion of the reduction, the reaction mixture was treated in the same manner as in Example 1 to obtain 9.91 g of N-acetylphenylalanine as a white crystal. Its melting point was 149.5°-150.5° C.

Workup

  1. customIn a 100-ml tightly-sealed glass vessel

Sources & evidence

ORD record
ord-76e574437a3346ffb9e6a4987fee15f3
Source dataset
uspto-grants-1986_09
Patent number
US04612388

Linked notes

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