HCID 67170224, compound → HCID 52916808, compound

(2R,3R)-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-b2f58023753d4181b54df105f0bff77b

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09272983B2