Thionyl Chloride → HCID 22258070, compound

Participants

Reaction Steps

To a stirred solution of Example 1 Part B compound (1.009 g, 2.19 mmol) in CH2Cl2 (20 mL) under argon at room temperature was added a solution prepared from benzotriazole (570 mg, 4.8 mmol) and thionyl chloride (570 mg, 4.8 mmol) in CH2Cl2 (5 mL) over 2 min. The reaction mixture was stirred for 90 min, then diluted with water and extracted twice with CH2Cl2. The extracts were combined, washed once with water, once with 0.5 M NaOH (25 mL) and once with brine, dried (MgSO4) and evaporated. The residuum was immediately dissolved in DMF (8 mL), treated with sodium azide (570 mg, 8.8 mmol) and stirred at room temperature under argon for 1 h. The reaction mixture was quenched with water and extracted twice with Et2O. The extracts were combined, washed twice with water, once with brine dried (MgSO4) and evaporated. Purification by flash chromatography on silica gel provided the title compound as a colorless oil, 657 mg (62% yield). LC/MS gave the correct molecular ion [(M+H)+=486] for the desired compound.

Provenance & Evidence