tert-Butyldimethylsilane → HCID 58997398, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the title C compound, (S)-2-acetylamino-N-((S)-2-{4-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-3-phenyl-propionamide (49 mg, 0.07 mmol) in TFA (1.4 mL) containing t-butyldimethylsilane (0.035 mL, 0.21 mmol) is heated at 80° C. for 1 h. The reaction is concentrated under nitrogen stream to give an oil which is taken up in 60% MeCN in water. Water (1 mL) is added, and the mixture filtered through a 0.1 micron Acrodisc filter. The resulting mixture is loaded onto a preparative reverse phase HPLC column (YMC CombiPrep Pro C18, 50×20 mm I.D., particle size S-5 micron, 12 nM) in three aliquots and eluted at 30 mL/min with a gradient of 90:10 (0.1% TFA in water:MeCN) to 10:90 over 5 min. Then held at 10:90 until 7 min. Fractions containing product are combined and concentrated on a Savant Speedvac to yield (S)-2-acetylamino-N-((S)-1-pentylcarbamoyl-2-[4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl)-3-phenyl-propionamide as a white solid: [M−1]−=556.

Provenance & Evidence