Pyruvic Acid → (2S)-2-[[(2S)-1-ethoxy-1-oxopentan-2-yl]amino]propanoic acid

L-Norvaline ethyl ester hydrochloride (50 gm) was dissolved in ethanol (600 ml). Sodium hydroxide (15.4 gm) dissolved in ethanol (500 ml) was added to the above at 10° C. and stirred for 30 minutes. Pyruvic acid (34.5 gm) solution in ethanol (200 ml) was then added to above reaction mass at 10° C. and stirred for 30 minutes. The reaction mass was then transferred to a hydrogenator along with 10% palladium on carbon (5 gm) and hydrogenated at 7 bar for 8 hours. The contents were filtered over celite and washed with ethanol (200 ml). The filtrate was concentrated completely under vacuum at about 50° C. Acetone (800 ml) was added to the residue and the contents refluxed for 1 hour and then cooled to room temperature and filtered to obtain the product (30 gm) as white crystals.

1. additionwas added to the above at 10° C.
2. stirringstirred for 30 minutes
3. filtrationThe contents were filtered over celite
4. washwashed with ethanol (200 ml)
5. concentrationThe filtrate was concentrated completely under vacuum at about 50° C
6. additionAcetone (800 ml) was added to the residue
7. temperaturethe contents refluxed for 1 hour
8. filtrationfiltered

ORD record

ord-0b083cf0231345e99b7a4705e7f8b55d

Source dataset

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07666896B2