Triethylamine → HCID 59242738, compound

Participants

Reaction Steps

Slowly add diphenylphosphorylazide (5.45 g, 4.27 mL, 19.8 mmol) to a refluxing mixture of 5-((S)-7-cyano-2-isopropoxycarbonylamino-2,3-dihydro-1H-cyclopenta[b]indol-4-ylmethyl)-thiazole-4-carboxylic acid (3.82 g, 9.00 mmol), Et3N (2.00 g, 2.76 mL, 19.8 mmol), and 2-(trimethylsilyl)-ethanol (10 mL, 8.25 g, 69.8 mmol) in toluene (270 mL). Continue at reflux for 3 h, then cool to room temperature. Concentrate the reaction mixture to give 14.85 g crude. Purify on silica gel (115 g) using 20-60% EtOAc/hexanes to give 4.06 g (84%) of the product as a yellow solid. LC-ES/MS m/z 562 (M+Na), 538 (M−H), TR=3.1 min.

Provenance & Evidence