Methyl 3-oxovalerate → Methyl (2Z)-3-amino-2-pentenoate

A mixture of methyl 3-oxovalerate (75.0 g, 576 mmol), ammonium acetate (222 g, 2.88 mol) and methanol (750 mL) was stirred at room temperature for 3 days. The mixture was concentrated under reduced pressure, water (500 mL) was added to the residue and the mixture was extracted with ethyl acetate (200 mL). The extract was washed with brine, dried over magnesium sulfate, concentrated under reduced pressure, and dried to give the title compound (68.5 g, 92%) as a pale-yellow oil.

1. concentrationThe mixture was concentrated under reduced pressure, water (500 mL)
2. additionwas added to the residue
3. extractionthe mixture was extracted with ethyl acetate (200 mL)
4. washThe extract was washed with brine
5. dry with materialdried over magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customdried

ORD record

ord-9fed9123cc1045a8b0d04c0d41fb45bf

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08217176B2