Triethylamine → Ethyl 2-butyramido-3-mercaptopropanoate

Triethylamine (4.5 mL) was added to a suspension of ethyl 2-amino-3-mercaptopropanoate hydrochloride (5 g) in DCM (50 mL). The resulting mixture was cooled in an ice/salt bath and butyryl chloride (3.3 mL) was added dropwise. The resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated sodium bicarbonate solution (50 mL) and the layers separated. The aqueous phase was extracted with DCM (2×100 mL). The combined organic solutions were washed with brine (100 mL), dried over sodium sulphate, filtered and evaporated. The resulting white solid was purified by silica gel chromatography eluting with 4:1 to 1:1 isohexane:ethyl acetate gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a white solid. Yield 3 g.

1. temperatureThe resulting mixture was cooled in an ice/salt bath
2. customThe reaction was quenched with saturated sodium bicarbonate solution (50 mL)
3. customthe layers separated
4. extractionThe aqueous phase was extracted with DCM (2×100 mL)
5. washThe combined organic solutions were washed with brine (100 mL)
6. dry with materialdried over sodium sulphate
7. filtrationfiltered
8. customevaporated
9. customThe resulting white solid was purified by silica gel chromatography
10. washeluting with 4:1 to 1:1 isohexane
11. additionThe fractions containing product
12. customevaporated

ORD record

ord-cccef92026d74d02a6f8ea601a72ac25

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2