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

CDI (8.5 g) was added to a solution of cyclopentanecarboxylic acid (5.2 mL) in DMF (40 mL). The resulting mixture was stirred for 1 h and cooled in an ice bath. Ethyl 2-amino-3-mercaptopropanoate hydrochloride (8.88 g) was added, followed by triethylamine (10 mL). 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 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 solid was purified by silica gel chromatography eluting with 4:1 to 1:1 isohexane:ethyl acetate gradient. The fractions containing the product were combined and evaporated to give the subtitled compound as a white solid. Yield 7.7 g.

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

ORD record

ord-d1eacc02a610405bb3ed289ad11d0017

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08476265B2