Methanol → (1R,2S)-1-(((1,1-Dimethylethoxy)carbonyl)amino)-2-ethenylcyclopropanecarboxylic acid

Temperature

45 °C

A round-bottom flask was charged with (1R,2S)-ethyl 1-((tert-butoxycarbonyl)amino)-2-vinylcyclopropanecarboxylate (4 g, 15.67 mmol) and lithium hydroxide monohydrate (2.63 g, 62.7 mmol). Methanol (52.2 ml), THF (52.2 ml) and water (52.2 ml) were added. The mixture was heated (oil bath at 45° C.) overnight. The reaction mixture was concentrated to half-its volume in rotavap and the pH of the mixture was adjusted to pH=2-3 with aq 1M HCl. The mixture was extracted with dichloromethane (3×150 mL). The combined organic extracts were washed with brine (50 mL), dried over magnesium sulfate, filtered and concentrated in rotavap to give the title compound (3.5 g, 15.40 mmol, 98% yield) as a white powder. No further purification was carried out.

1. concentrationThe reaction mixture was concentrated to half-its volume in rotavap
2. extractionThe mixture was extracted with dichloromethane (3×150 mL)
3. washThe combined organic extracts were washed with brine (50 mL)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in rotavap

ORD record

ord-19565a8cd2074a4aaf9b61661348ae9e

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09328138B2