Hydrochloric Acid → tert-butyl 6-(8-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydroisoquinolin-2(1H)-yl)-3-(3-oxopropyl)picolinate

Participants

Reaction Conditions

Reaction Steps

Compound 96A (7.58 g) was dissolved in THF (120 mL). To this solution was added 5% aq. HCl (100 mL). The reaction mixture was heated at 48° C. for 90 min. After cooling to room temperature, the reaction mixture was quenched with sat. NaHCO3 solution until no more CO2 was released. The solution was concentrated under vacuum. The residue was re-dissolved in EtOAc, and treated with water (500 mL). The organic layer was separated, and the aqueous layer was extracted with additional EtOAc (three times). The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated under vacuum. The residue was purified with flash column chromatography on silica gel eluting with 7:3/Hex:EtOAc to give 5.5 g of the title compound 96B (78%): APCI (+)LC/MS: 543 (M+H)+.

Provenance & Evidence