tert-Butyldimethylsilane → HCID 58997413, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the title H compound, (S)-2-acetylamino-N-((S)-2-{3-[5-(4-methoxy-benzyl)-1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl]-phenyl}-1-pentylcarbamoyl-ethyl)-3-phenyl-propionamide (124 mg, 0.183 mmol) in TFA (3 mL) containing t-butyidimethylsilane (0.091 mL, 0.548 mmol) is heated at 80° C. for 30 min, then concentrated under nitrogen stream to give an oil containing a fine dark suspension. The product is taken up in 60% MeCN in water and water (1 mL) is added. The mixture filtered through a 0.1 micron Acrodisc filter and the filtrate 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 five 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-[3-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-phenyl]-ethyl}-3-phenyl-propionamide as a white foam: [M+1]+=558.

Provenance & Evidence