Acetone → HCID 178454715, compound

Temperature

10 °C

Agmatine sulfate (100 g, 397 mmol) was dissolved in 400 mL of aqueous 1.00 N NaOH. Acetone (200 mL) was then added and the stirred mixture was cooled to about 10° C. in a cold water bath. An additional 80 mL of H2O was added to keep the agmatine sulfate in solution. 2-isocyanatoethyl methacrylate (58.0 mL, 411 mmol) was then added to the reaction mixture, via an addition funnel, over a period of 30 min. After stirring an additional 45 min, the reaction mixture was placed on a rotary evaporator at ambient temperature. After pulling off most of the acetone, the reaction mixture was transferred to a separatory funnel and washed with ethyl acetate (2×250 mL) and methylene chloride (2×200 mL). The remaining aqueous solution was adjusted to pH 7 by addition of a small amount of dilute sulfuric acid and then placed on a rotary evaporator at ambient temperature to draw off any remaining volatiles. Lyophilization yielded the title compound (162 g) as a white powder. 1H NMR (500 MHz, D2O) δ 6.14 (s, 1H), 5.73 (s, 1H), 4.23 (t, J=5.2 Hz, 2H), 3.45 (t, J=5.4 Hz, 2H), 3.18 (t, J=7.0 Hz, 2H), 3.12 (t, J=6.4 Hz, 2H), 1.22 (s, 3H), 1.61-1.48 (m, 4H).

1. customthe reaction mixture was placed on a rotary evaporator at ambient temperature
2. customthe reaction mixture was transferred to a separatory funnel
3. washwashed with ethyl acetate (2×250 mL) and methylene chloride (2×200 mL)
4. additionThe remaining aqueous solution was adjusted to pH 7 by addition of a small amount of dilute sulfuric acid
5. customplaced on a rotary evaporator at ambient temperature

ORD record

ord-7a1c50f5119a4946ab54695bcee2ec8d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272246B2