Triethylamine → Ethyl 2-(cyclopropanecarboxamido)-3-mercaptopropanoate

Cyclopropanecarbonyl chloride (3.1 mL) was added to a suspension of triethylamine (4.68 mL) and ethyl 2-amino-3-mercaptopropanoate hydrochloride (5.2 g) in DCM (200 mL) at 0° C. The resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with ethanol and the solvent evaporated. The residue was suspended in ethyl acetate (200 mL) and washed with saturated sodium bicarbonate solution (2×150 mL), aqueous HCl solution (2M, 2×150 mL) and brine (150 mL), then dried over magnesium sulphate, filtered and evaporated. The resulting white solid was purified by silica gel chromatography eluting with 4:1 isohexane:ethyl acetate to give the subtitled compound as a white solid. Yield 5 g.

1. customThe reaction was quenched with ethanol
2. customthe solvent evaporated
3. washwashed with saturated sodium bicarbonate solution (2×150 mL), aqueous HCl solution (2M, 2×150 mL) and brine (150 mL)
4. dry with materialdried over magnesium sulphate
5. filtrationfiltered
6. customevaporated
7. customThe resulting white solid was purified by silica gel chromatography
8. washeluting with 4:1 isohexane

ORD record

ord-65c0d4117133428aa46748f1ce0a26f8

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629271B2