Ethyl Acetate → HCID 12807303, compound

1 liter of ethyl acetate was added to 80 g of BOC-Val.DCHA and the mixture was washed twice with 600 ml of sulfuric acid and water, dried over anhydrous sodium sulfate and concentrated in vacuo to obtain the free acidin an oily form. The free acid and 28 g of H-Gly-OEt.HCl were dissolved in a solvent mixture of 150 ml of chloroform and 150 ml of THF. The solution was cooled and 28 ml of triethylamine and 41.2 g of DCC were added thereto. The resultant mixture was stirred at a temperature of 0° to -2° C. for 1 hour and at room temperature overnight. The insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1 N hydrochloric acid, water, a 5% sodium bicarbonate aqueous solution and water, dried over magnesium sulfate and concentrated in vacuo. The resulting residue was crystallized by addition of n-hexane and recrystallized from ethyl acetate-diethyl ether-n-hexane to obtain 54 g (89.2%) of the desired material with a melting point of 94°-96° C.

1. washDCHA and the mixture was washed twice with 600 ml of sulfuric acid and water
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated in vacuo
4. customto obtain the free acidin an oily form
5. temperatureThe solution was cooled
6. customThe insoluble materials were removed by filtration
7. concentrationthe filtrate was concentrated in vacuo
8. dissolutionThe residue was dissolved in ethyl acetate
9. washwashed with 1 N hydrochloric acid, water
10. dry with materiala 5% sodium bicarbonate aqueous solution and water, dried over magnesium sulfate
11. concentrationconcentrated in vacuo
12. customThe resulting residue was crystallized by addition of n-hexane
13. customrecrystallized from ethyl acetate-diethyl ether-n-hexane

ORD record

ord-4db5c50d0d1149369e3378b6889c7402

Source dataset

uspto-grants-1981_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04277393