Water → HCID 178472215, compound

To a solution of ethyl-3-aminocrotonate (F-1) (64.6 g, 0.5 mol, 1.0 eq) and pyridine (44.5 mL, 0.55 mol, 1.1 eq) in THF (600 mL) at −20° C., 2-chloroacetyl chloride (59.3 g, 0.53 mol, 1.05 eq) is added dropwise within 1 h. The resulting mixture is stirred from −20° C. to RT for an additional 2 h and then it is poured into H2O (1200 mL). The mixture is extracted with ethyl acetate (3×1200 mL). The combined organic layer is washed with H2O (2×500 mL) and brine (500 mL), dried over anhydrous Na2SO4 and filtered. The filtrate is concentrated in vacuo to reduce the volume to about 200 mL. The residue is slurried in petroether (400 mL) at RT for 30 min. The solid is collected by filtration, rinsed with petroether (200 mL), and dried in vacuo to afford the product, (E)-ethyl 3-amino-2-(2-chloroacetyl)but-2-enoate (F-2).

1. extractionThe mixture is extracted with ethyl acetate (3×1200 mL)
2. washThe combined organic layer is washed with H2O (2×500 mL) and brine (500 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationThe filtrate is concentrated in vacuo
6. waitThe residue is slurried in petroether (400 mL) at RT for 30 min
7. filtrationThe solid is collected by filtration
8. washrinsed with petroether (200 mL)
9. customdried in vacuo

ORD record

ord-c140343dd2ef4af386db6cdaf1b2ccf8

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08969363B2