Water → HCID 118157132, compound

Participants

Reaction Steps

(2S,3S,E)-tert-Butyl 3-((S)-3-(4-(but-2-ynyloxy)phenyl)-1-(2-hydroxyethylamino)-1-oxopropan-2-ylcarbamoyl)-11-(2-heptyl-1,3-dioxolan-2-yl)-2-hydroxy-2-(2-methoxyethyl)undec-4-enoate (11.3 mg, 0.014 mmol) was dissolved in dichloromethane (0.5 mL), and water (50 μL) was added. Trifluoroacetic acid (1.5 mL) was further added. The reaction mixture was stirred at room temperature for 5 hours, and then concentrated. The resulting residue was dissolved in methanol (1.0 mL). To the solution was added an aqueous solution (50 μL) of 28% ammonia and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated, and the resulting residue was then diluted in ethyl acetate, and washed with an aqueous solution of 0.5 M citric acid. The separated organic layer was washed with a saturated brine, dried over anhydrous sodium sulfate, then filtered, and concentrated. The resulting residue was purified by diol silica gel thin layer chromatography (dichloromethane/methanol) to obtain the target compound as colorless oil at a yield of 80%.

Provenance & Evidence