Hydrochloric Acid → HCID 14329788, compound

To a solution of (E,E)-4-ethyl-2,4-hexadienoic acid (2.8 g) and N-hydroxysuccinimide (2.3 g) in dioxane (20 ml) was added dicyclohexylcarbodiimide (4.32 g). The mixture was stirred at ambient temperature overnight and then filtered. The filtrate was concentrated to dryness under reduced pressure to give a residue which was dissolved in tetrahydrofuran (100 ml). To the solution was added a solution of glycine (4.5 g) and triethylamine (8.34 ml) in water (60 ml). The resulting mixture was stirred at ambient temperature for 5 hours, acidified with 1N hydrochloric acid and then extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and then concentrated to dryness under reduced pressure to give a crystalline residue. The residue was triturated with a mixture of chloroform and hexane to give N-[(E,E)-4-ethyl-2,4-hexadienoyl]glycine (1.72 g).

1. filtrationfiltered
2. concentrationThe filtrate was concentrated to dryness under reduced pressure
3. customto give a residue which
4. stirringThe resulting mixture was stirred at ambient temperature for 5 hours
5. extractionextracted with ethyl acetate
6. washThe extract was washed with water
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated to dryness under reduced pressure
9. customto give a crystalline residue
10. customThe residue was triturated with a mixture of chloroform and hexane

ORD record

ord-a83bf4d2e2f34a0ab84a4c872f2a2e32

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04782088