Hydrochloric Acid → HCID 89699859, compound

Participants

Reaction Steps

Under argon, 1.25 g (4.73 mmol) of the compound of Example 24A were combined with 1.46 g (6.2 mmol) of tert-butyl (3-bromopropyl)carbamate and 4.62 g (14.2 mmol) of caesium carbonate in 25 ml of DMF and stirred at RT until the reaction had gone to completion. The reaction was then acidified with 4 M hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and concentrated under reduced pressure. The residue was taken up in 25 ml of THF and 12 ml of water and, after addition of 596 mg (14.2 mmol) of lithium hydroxide monohydrate, stirred at 40° C. for 4 h. After the reaction had ended, water and ethyl acetate were added and the mixture was adjusted to pH 2 with 1 M hydrochloric acid. The organic phase was separated off, dried over magnesium sulphate, filtered and concentrated on a rotary evaporator. The crude product was purified by preparative HPLC (Method 19). This gave 1.64 g (92% pure, 76% of theory) of the title compound.

Provenance & Evidence