Compounds for proteasome enzyme inhibition
A compound, alkyl technology for enzyme inhibition-based therapeutics addressing issues of lack of specificity, stability or potency
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[0222] Scenario 1: Example 1 Synthesis
[0223]
[0224] (B) Synthesis
[0225]HOBT (10.81 g, 80.0 mmol) and DIEA (200.0 mmol, 25.85 g , 35mL). The mixture was cooled to 0°C in an ice bath, and BOP (80.0 mmol, 35.38 g) was added in portions over 5 minutes. The reaction solution was placed under an argon atmosphere and stirred overnight. The reaction was diluted with brine (1000 mL), and extracted with ethyl acetate (5 x 200 mL). The combined organic layers were washed with water (10 x 100 mL) and brine (2 x 150 mL), dried over magnesium sulfate. Magnesium sulfate was removed by filtration and volatiles were removed under reduced pressure to afford (A) (18.17g). BocNHLeuPheOMe (45.86 mmol, 18.0 g) was added to 50 mL of 80% TFA / DCM solution cooled at 0°C. The solution was stirred and allowed to warm to room temperature over 2 hours. The volatiles were removed under reduced pressure to give an oil. To this oil was added BocNHhPhe (45.86 mmol, 12.81 g), DMF (500 mL), H...
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