Ethylamine → S-methyl-N-butyloxycarbonyl-L-cysteine ethylamide

Temperature

-15 °C

S-Methyl-N-t-butyloxycarbonyl-L-cysteine (6.63 g, 28.2 mmole) was dissolved in 70 ml of tetrahydrofuran and 4.18 ml (30 mmole) of triethylamine was added to the solution. To the resulting mixture was added dropwise 3.94 ml (30 mmole) of isobutyl chloroformate under cooling at -15° C. and the mixture was stirred at that temperature for 20 minutes. After cooling to -40° C., 3.9 g (60 mmole) of aqueous 70% ethylamine solution was added in a portion and the mixture was stirred for 3 hours under ice cooling. Thereafter, 30 ml of aqueous 5% sodium bicarbonate was added and the organic layer was separated. The aqueous layer was then extracted with 50 ml of ethyl acetate and the combined organic layers were washed successively with 30 ml of aqueous 5% sodium bicarbonate, 30 ml of aqueous saturated sodium chloride, 30 ml of aqueous 10% citric acid, 30 ml of aqueous 5% sodium bicarbonate and 30 ml of aqueous saturated sodium chloride and dried over anhydrous magnesium sulfate. The solution was then concentrated in vacuo, resulting in formation of crystals, which were collected and recrystallized from ethyl acetate-n-hexane to give 5.17 g of S-methyl-N-butyloxycarbonyl-L-cysteine ethylamide (70% yield), m.p. 106°-7° C.

1. temperatureAfter cooling to -40° C.
2. stirringthe mixture was stirred for 3 hours under ice cooling
3. customthe organic layer was separated
4. extractionThe aqueous layer was then extracted with 50 ml of ethyl acetate
5. washthe combined organic layers were washed successively with 30 ml of aqueous 5% sodium bicarbonate, 30 ml of aqueous saturated sodium chloride, 30 ml of aqueous 10% citric acid, 30 ml of aqueous 5% sodium bicarbonate and 30 ml of aqueous saturated sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationThe solution was then concentrated in vacuo
8. customresulting in formation of crystals, which
9. customwere collected
10. customrecrystallized from ethyl acetate-n-hexane

ORD record

ord-929b17faca9e49239f717ffb60226f89

Source dataset

uspto-grants-1984_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04440788