Water → HCID 52918570, compound

Participants

Reaction Conditions

Reaction Steps

1.50 g (2.97 mmol) of methyl 3-(4-chloro-3-{[(2S,3R)-2-(4-chlorophenyl)-4,4,4-trifluoro-3-methylbutanoyl]amino}phenyl)hexanoate (diastereomer mixture) were dissolved in 5 ml of acetic acid, 5 ml of 30% strength sulphuric acid were added and the mixture was heated at reflux (bath temperature about 140° C.). After 1.5 h, a further 2.5 ml of acetic acid were added, and the reaction mixture was stirred under reflux for another 2.5 h. After cooling, the mixture was allowed to stand at RT overnight, then added to water and extracted three times with ethyl acetate. The combined organic phases were washed with 5% strength sodium bicarbonate solution and sat. sodium chloride solution, dried over magnesium sulphate and concentrated under reduced pressure, and the residue was dried under high vacuum. This gave 1.44 g of the target product (98.8% of theory).

Provenance & Evidence