Sodium Iodide → HCID 89955667, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (3S)-3-(3-chloro-5-(4-(Methoxymethyl)tetrahydro-2H-pyran-4-yl)phenyl)-3-(2-(3-hydroxy-5-((5-hydroxy-1,4,5,6-tetrahydropyrimidin-2-yl)amino)benzamido)acetamido)propanoic acid TFA salt (Example 16) (85.5 mg, 0.117 mmol) in anhydrous dichloromethane (2.0 mL) was added a solution of 15-crown-5 (155.0 mg, 0.702 mmol) saturated with sodium iodide in dichloromethane (6.0 mL) at room temperature and the reaction mixture was cooled to −30° C. (dry-ice/CH3CN) and a 1.0 M BBr3 solution in dichloromethane (350 μL, 0.35 mmol) was added and the reaction mixture stirred at −30° C. for 2 h to give an orange suspension. After 2 hr the reaction mixture was allowed to warm slowly to room temperature and stirred at room temperature overnight to give an orange-cream suspension. The suspension was filtered, washed with dichloromethane (2×10 mL) and dried in vacuo to give a yellow-cream solid. The crude product was purified by reverse-phase HPLC with a gradient 10-50% CH3CN in water containing 0.05% TFA to give the desired product (Example 17), after lyophilization, as a colorless lyophilized solid (64.5 mg). LC/MS analysis of the product shows the desired product's mass: m/z 604 (35ClM+H), m/z 606 (37ClM+H), m/z 626 (35ClM+Na), and m/z 628 (37ClM+Na), Calcd for C28H34ClN5O8:604.05.

Provenance & Evidence