Water → HCID 22174526, compound

Participants

Reaction Steps

Compound 198 (100 mg, 0.25 mmol) was dissolved in dry pyridine (130 μL) under an argon atmosphere. The solution was cooled on an ice bath and 4-toluenesulfonyl chloride (48 mg, 0.25 mmol) was added. The reaction mixture was quenched with water after 45 min at room temperature. The aqueous phase was extracted twice with EtOAc. The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/EtOAc 4:1 as the eluent. The tosylate was dissolved in dry DMF (2.0 mL) and morpholine (17 μL, 0.19 mmol) was added. The reaction mixture was stirred for 48 h at room temperature and then poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with water, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using DCM/MeOH 100:4 as the eluent to afford the title compound as a yellow oil.

Provenance & Evidence