Ethyl Acrylate → HCID 118045370, compound

Temperature

0 °C

To tert-butyl 5-(cyanomethyl)pyrazin-2-ylcarbamate (0.32 g, 1.37 mmol) in a mixture solvent of ethanol/2-methyltetrahydrofuran (5 mL/5 mL) was added freshly prepared sodium ethoxide (1 M, 1.366 mL), and the mixture was stirred at 0° C. for 10 min, followed by addition of ethyl acrylate (145 ul, 1.366 mmol) and the mixture was stirred at 0° C. for 2 h. The reaction was quenched at this point by adding sat. NaHCO3 (5 mL), and the reaction mixture was stirred for another 10 min, diluted with EtOAc (20 mL), filtered and the filtrate was concentrated. The residue was dissolved in EtOAc (20 mL), washed with pH 7.0 sodium phosphate buffer, and EtOAc layer was concentrated, and the light brown residual oil was purified by flash column eluted with gradient EtOAc/heptane (0-50%) to afford ethyl 4-(5-(tert-butoxycarbonylamino)pyrazin-2-yl)-4-cyanobutanoate (100 mg, 22% yield). LCMS (m/z): 279.2 (MH+-tBu), 0.86 min.

1. stirringthe mixture was stirred at 0° C. for 2 h
2. customThe reaction was quenched at this point
3. additionby adding sat. NaHCO3 (5 mL)
4. stirringthe reaction mixture was stirred for another 10 min
5. additiondiluted with EtOAc (20 mL)
6. filtrationfiltered
7. concentrationthe filtrate was concentrated
8. dissolutionThe residue was dissolved in EtOAc (20 mL)
9. washwashed with pH 7.0 sodium phosphate buffer, and EtOAc layer
10. concentrationwas concentrated
11. customthe light brown residual oil was purified by flash column
12. washeluted with gradient EtOAc/heptane (0-50%)

ORD record

ord-4a6411f119bc4de89df7df4415f4f23d

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242996B2