Acetaldehyde → L-Alanine

Temperature

250 °C

0.10 mol of acetaldehyde and 0.20 mol of L-menthoxyacetamide are heated together at 100° C. with stirring, and the product solid is heated in a sublimator at 250° C. and 1 mm Hg until formation of the enamide L-(menthoxyacetylamino)ethene is complete. A 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar is charged with THF (5 mL), methanol (20 μL, 0.5 mmol), Co2 (CO)8 (0.05 mmol), pyridine (0.25 mmol,) and L-(menthoxyacetylamino)ethene (0.5 mmol.) The reactor is sealed, pressurized to 1000 psig with CO, and the reaction mixture is stirred for 24 hours at 100° C. The product mixture, isolated after removal of gas from the reactor vessel, contains a mixture of N-(L-menthoxyacetyl)-D-alanine methyl ester and N-(L-menthoxyacetyl)-L-alanine methyl ester. Separation of these products is effected by silica gel chromatography with ether-toluene eluent, and the diastereomers are treated separately with 2N HCl solution at 100° C. for 3 hours to give pure L-alanine and D-alanine.

1. customA 70 mL stainless steel high pressure reactor fitted with a Pyrex glass liner and magnetic stir bar
2. customis sealed
3. stirringthe reaction mixture is stirred for 24 hours at 100° C
4. customThe product mixture, isolated
5. customafter removal of gas from the reactor vessel
6. additiona mixture of N-(L-menthoxyacetyl)-D-alanine methyl ester and N-(L-menthoxyacetyl)-L-alanine methyl ester
7. customSeparation of these products
8. additionthe diastereomers are treated separately with 2N HCl solution at 100° C. for 3 hours

ORD record

ord-48102df380314949ae75316febd6d61e

Source dataset

uspto-grants-1990_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04929755