Acetone → HCID 11298255, compound

Temperature

40 °C

10.0 g (0.06 mol) of 2-methylcysteinamide hydrochloride as a racemic body was dissolved in 300 ml of water, and the obtained solution was then placed in a 500-ml flask. Thereafter, an aqueous manganese chloride solution was added thereto, such that the concentration of divalent Mn ions became 10 ppm. Thereafter, intact cells corresponding to 1.0 g of dried cells were further added thereto. The mixture was stirred at 40° C. for 24 hours under nitrogen flow, so as to carry out hydrolysis. After completion of the reaction, the cells were removed from the reaction solution by centrifugation to obtain a supernatant. This supernatant was concentrated using a rotary evaporator, and the concentrate was then dissolved in 150 ml of methanol. Subsequently, 200 ml of acetone and 3.6 g (0.03 mol) of sodium carbonate were added thereto, and the mixture was stirred at room temperature for 16 hours, so as to carry out the reaction. Thereafter, the reaction solution was concentrated, and then supplemented with 50 ml of isobutyl alcohol and subjected to reflux conditions for 4 hours so as to extract soluble matters. After cooling, crystals that remained as insoluble matters were separated by filtration. The obtained filtrate was concentrated and dried using a rotary evaporator. The obtained concentrate was washed with 50 ml of hexane and then dried again to obtain 2,2,4-trimethylthiazolidine-4-carboxamide as a white solid. The obtained 2,2,4-trimethylthiazolidine-4-carboxamide was suspended in 100 ml of pure water, and was heated to reflux for 3 hours. Thereafter, the reaction solution was washed with 50 ml of diethyl ether twice. A water layer thereof was concentrated and dried, followed by drying under reduced pressure, to obtain 3.3 g (0.02 mol) of 2-methyl-D-cysteine. The yield of isolation was found to be 84 mol % relative to 2-methyl-D-cysteinamide contained in the racemic body that had been used for the reaction, and was found to be 42 mol % relative to 2-methylcysteinamide as a racemic body. Moreover, this solid was analyzed by liquid chromatography using an optical isomer separation column. As a result, the optical purity thereof was found to be 95% e.e. or more.

1. customthe obtained solution was then placed in a 500-ml flask
2. additionThereafter, intact cells corresponding to 1.0 g of dried cells were further added
3. customhydrolysis
4. customAfter completion of the reaction
5. customthe cells were removed from the reaction solution by centrifugation
6. customto obtain a supernatant
7. concentrationThis supernatant was concentrated
8. customa rotary evaporator
9. dissolutionthe concentrate was then dissolved in 150 ml of methanol
10. stirringthe mixture was stirred at room temperature for 16 hours
11. customthe reaction
12. concentrationThereafter, the reaction solution was concentrated
13. temperatureto reflux conditions for 4 hours so as
14. extractionto extract soluble matters
15. temperatureAfter cooling
16. customwere separated by filtration
17. concentrationThe obtained filtrate was concentrated
18. customdried
19. customa rotary evaporator
20. concentrationThe obtained concentrate
21. washwas washed with 50 ml of hexane
22. customdried again

ORD record

ord-8e53d69aea3c4201bee1455eeddf9848

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07470525B2