SYNTHESIS OF $alpha$-DL-ALANINE-2-C$sup 1$$sup 4$

Journal Article · Tue Oct 01 04:00:00 EDT 1963 · Pharmazie (West Germany)

OSTI ID:4030925

Bubner, M; Schmidt, L H

BS>A multistep synthesis of alanine-2-/sup 14/C in 32 to 47% overall yield based on starting Na acetate-/sup 14/C is described. High yields are obtained by the use of high vacuum techniques, and the apparatus is illustrated. Na acetate-1-/sup 14/C is acidified with HCl to yield acetic acid-l-/sup 14/C in 99% yield. This is converted to acetyl chloride in 97.0% yield by the use of phthaloyl chloride at 80 deg C. The acetyl chloride-1-/sup 14/C is reduced with 2N LiAlH/sub 4/ in diethylene glycol-diethyl ether at 0 deg C, giving ethanol-1-/ sup 14/C in 88% yield. The alcohol is next converted into ethyl iodide-1-/sup 14/ C with HI at 110--130 deg C; the yield is 71% based on Na acetate, The ethyl iodide is converted to the Grignard reagent and carbonated to yield (as the isolated product) sodium propionate-2-/sup 14/C in 81% yield (based on ethyl iodide, or 58% based on Na acetate). The salt is converted into the free acid in the fashion described for acetic acid, and this is treated with red P and Br/sup 2/ to yield alpha -bromopropionic acid-2-/sup 14/C in 52% yield (based on Na acetate). Treatment of this with ammonium carbonate-- aqueous ammonia at temperatures not over 60 deg C yields alpha -DL-alanine-2-/sup 14/C in 79% yield (based on bromoacid; 41% based on Na acetate) after purification on a Wofatit F column and sublimation. No further impurities could be detected by paper chromatography. Alanine labelled in the one or three position may be prepared in an analogous fashion. (BBB)

• Research Organization: Zentralinstitut fur Kernphysik, Rossendorf, Ger.
• NSA Number: NSA-18-020033
• OSTI ID: 4030925
• Journal Information: Pharmazie (West Germany), Journal Name: Pharmazie (West Germany) Vol. Vol: 18; ISSN PHARA
• Country of Publication: Country unknown/Code not available
• Language: German

Related Subjects

ACETATES
ACETIC ACID
ACETYL RADICALS
ACIDITY
ALANINE
ALCOHOLS
ALLOTROPY
ALUMINUM HYDRIDES
AMINO ACIDS
AMMONIA
AMMONIUM COMPOUNDS
CARBON 14
CARBONATES
CHEMICAL REACTIONS
CHEMISTRY
CHLORIDES
ETHANOL
ETHERS
ETHYL RADICALS
ETHYLENE
EVAPORATION
GLYCOLS
GRIGNARD REAGENTS
HYDROCHLORIC ACID
IMPURITIES
IODIDES
ION EXCHANGE MATERIALS
LABELLED COMPOUNDS
LABORATORY EQUIPMENT
LITHIUM HYDRIDES
ORGANIC BROMINE COMPOUNDS
ORGANIC IODINE COMPOUNDS
ORGANOMETALLICS
PHOSPHORUS
PREPARATION
PROPIONIC ACID
REDUCTION
SODIUM COMPOUNDS
SOLIDIFICATION
SUBLIMATION
VACUUM