Hydrochloric Acid → ethyl (2RS)-2-acetylamino-3-(2-pyrazinyl)propanoate

HRID 47765Notes

Reaction equation

[OH-].[Na+].[C:3]([NH:6][C:7]([CH2:18][C:19]1[CH:24]=[N:23][CH:22]=[CH:21][N:20]=1)(C(OCC)=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4].Cl>C(O)C>[C:3]([NH:6][CH:7]([CH2:18][C:19]1[CH:24]=[N:23][CH:22]=[CH:21][N:20]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])(=[O:5])[CH3:4]

Participants

Conditions

Temperature: 20 °C

Procedure

12 cm3 of 6N sodium hydroxide are added dropwise to a solution of 14 g of diethyl 2-acetylamino-2-(2-pyrazinylmethyl)malonate in 240 cm3 of ethanol and the mixture is then stirred at a temperature in the region of 20° C. After 1 hour, the reaction medium is neutralized with 6 cm3 of 12N hydrochloric acid. After stirring for 2 hours at a temperature in the region of 20° C., the reaction medium is filtered and the filtrates are then concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C. The residue is taken up in 200 cm3 of dioxane, refluxed for 2 hours and concentrated as above. 8.5 g of ethyl (2RS)-2-acetylamino-3-(2-pyrazinyl)propanoate are obtained in the form of a cream-colored solid [1H NMR spectrum (300 MHz, (CD3)2SO-d6 δ in ppm): 1.13 (t, J=7 Hz: 3H); 1.80 (s: 3H); 3.12 (dd, J=14 and 8.5 Hz: 1H); 3.22 (dd, J=14 and 6 Hz: 1H); 4.07 (q, J=7 Hz: 2H); 4.71 (mt: 1H); 8.36 (d, J=8 Hz: 1H); 8.52 (d, J=2.5 Hz: 1H); from 8.55 to 8.65 (mt: 2H]).

Workup

stirringAfter stirring for 2 hours at a temperature in the region of 20° C.
filtrationthe reaction medium is filtered
concentrationthe filtrates are then concentrated under reduced pressure (1 kPa) at a temperature in the region of 40° C
temperaturerefluxed for 2 hours
concentrationconcentrated as above

Sources & evidence

ORD record: ord-2c67e2ef090f4202967442b4de552530
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699895B2

Reaction notes

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