Acetaldehyde → N-Acetyl-L-alanine

HRID 2073640Notes

Reaction equation

HRID 2073640 reaction equation
[CH:1](=O)C.[C:4]([NH2:7])(=[O:6])[CH3:5].[C:8]([O:11]CC)(=[O:10])[CH3:9]>[CH-]=O.[CH-]=O.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Co].[Co+2]>[C:4]([NH:7][C@H:9]([C:8]([OH:11])=[O:10])[CH3:1])(=[O:6])[CH3:5]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 178AcetamideHCID 8857Ethyl Acetate

Product 1

HCID 88064N-Acetyl-L-alanine

Reagents, catalysts & solvents 1

HCID 25049Dicobalt Octacarbonyl (stabilized with 1-5% Hexane)Catalyst

Conditions

Temperature
120 °C

Procedure

A 183 ml rocking autoclave equipped with a glass-liner, was charged with acetaldehyde (3.0 g), acetamide (5.9 g), ethyl acetate (15 g) and dicobalt octacarbonyl (0.34 g). The reaction was sealed and flushed with the mixture of CO-H2 (1:1 molar ratio). The system was pressured with CO-H2 (1:1 to 1200 psi and then pressured with pure CO to final pressure of 2300 psi. The autoclave was heated to 120° C. and held at this temperature for two hours. The system was allowed to cool to room temperature. The excess gas was vented. The resulting product mixture was liquid only. The cobalt analysis of this homogeneous solution was 4500 ppm (calculated 4800 ppm). The H-mmr analysis of the product solution indicated the presence of N-acetylalanine.

Workup

  1. customequipped with a glass-liner
  2. customThe reaction was sealed
  3. customflushed with the mixture of CO-H2 (1:1 molar ratio)
  4. temperatureto cool to room temperature

Sources & evidence

ORD record
ord-d1592c3ee7f94ab69b37aa76178eca07
Source dataset
uspto-grants-1990_04
Patent number
US04918222

Reaction notes

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