HCID 67169774, compound → HCID 52916807, compound

(2S,3S)-2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-hex-5-enoic acid methyl ester (2.01 g, 7.00 mmol) is dissolved in a 2:1 mixture of 6 N hydrochloric acid and glacial acetic acid (62.5 mL), and the solution is heated at reflux for 4 h. The solution is cooled to room temperature and concentrated under reduced pressure. The product is taken up in water and the solution is filtered. The filtrate is concentrated under reduced pressure and the residue is dissolved in water, then the solution is applied to a column of Amberlite™ IR 120 cation exchange resin (NH4+ form.). The column is washed with water (2.5 L), then eluted with aqueous ammonia solution (2.5 L). The eluate is boiled until no ammonia can be detected, then concentrated under reduced pressure affording the title compound (0.5 g, 3.50 mmol).

1. temperaturethe solution is heated
2. temperatureat reflux for 4 h
3. concentrationconcentrated under reduced pressure
4. filtrationthe solution is filtered
5. concentrationThe filtrate is concentrated under reduced pressure
6. dissolutionthe residue is dissolved in water
7. washThe column is washed with water (2.5 L)
8. washeluted with aqueous ammonia solution (2.5 L)
9. concentrationconcentrated under reduced pressure

ORD record

ord-81b9b74a83494417a55e8b97c97be20d

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272983B2