Dimethyl Sulfoxide → Aminoisobutyric acid

A mixture of 500 mg. (5.0 mmole) of 2-methylalanine and 800 mg. (5.0 mmole) of m-chlorobenzyl chloride in 10 ml. of dimethylsulfoxide is stirred at 60° C. for 6 hours and then allowed to cool to 20°-25° C. over 12 hours. Water, 150 ml., is added followed by a saturated sodium carbonate solution until a basic pH of 8 is obtained. The product is extracted into 50 ml. of ethyl ether which is then washed with four 25 ml. portions of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure (15-20 mm.) at 35°-40° C. The residue is converted into the hydrogen fumarate salt with 0.40 g. fumaric acid in 25 ml. 80% ethanol-20% ethyl acetate solution followed by precipitation with hexane. After filtering and drying, the m-chlorobenzyl ester of 2-methylalanine as the hydrogen fumarate salt containing one equivalent of fumaric acid as a co-precipitant, m.p. 144.0°-149.0° C., is obtained. Further recrystallization from the aforementioned ethanol-ethyl acetate-hexane system gives an analytical sample.

1. additionA mixture of 500 mg
2. temperatureto cool to 20°-25° C. over 12 hours
3. addition, is added
4. customis obtained
5. extractionThe product is extracted into 50 ml
6. washof ethyl ether which is then washed with four 25 ml
7. dry with materialportions of water, dried over anhydrous magnesium sulfate
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure (15-20 mm.) at 35°-40° C
10. custom80% ethanol-20% ethyl acetate solution followed by precipitation with hexane
11. filtrationAfter filtering
12. customdrying

ORD record

ord-2eff65259ba047dfbd4c926f4f95d3cf

Source dataset

uspto-grants-1976_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03988341