dimethyl 3-methyl-L-aspartate → (2S)-2-amino-4-methoxy-3-methyl-4-oxobutanoic acid

Temperature

70 °C

A mixture of dimethyl 3-methyl-L-aspartate (Preparation 64, 23 g, 82.55 mmol), CuCO3.Cu(OH)2 (21.9 g, 99.05 mmol) in water (250 mL) was heated to 70° C. for 4 hours. The resulting precipitate was filtered and the filtrate cooled to 0° C. Ammonium sulfide (20% in water, 67.5 mL, 198 mmol) was added slowly ensuring the temperature did not rise above 5° C. The reaction was filtered through arbocel to remove the copper residues and the filtrate concentrated in vacuo. The residue was redissolved in MeOH and filtered through arbocel, with concentration of the filtrate to dryness to afford the title compound as an oil that was used directly in the next step.

1. filtrationThe resulting precipitate was filtered
2. temperaturethe filtrate cooled to 0° C
3. customdid not rise above 5° C
4. filtrationThe reaction was filtered through arbocel
5. customto remove the copper residues
6. concentrationthe filtrate concentrated in vacuo
7. dissolutionThe residue was redissolved in MeOH
8. filtrationfiltered through arbocel, with concentration of the filtrate to dryness

ORD record

ord-aa131b17a9a447f68494f857fa7965ea

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927587B2