Ethanol → HCID 59161323, compound

Participants

Reaction Steps

Combine (R)-N-(9-(3-fluorobenzyl)-6-isobutyrylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxylic acid (Example 188) (0.281 g, 0.67 mmol) with diphenylphosphorylazide (1.3 ml, 0.67 mmol), and triethylamine (0.73 mL, 0.67 mmol) in benzene (3 mL) and heat at reflux for 18 h. Add absolute ethanol and heat for 4 h longer. Concentrate in vacuo, and partition the resulting residue between EtOAc and water. Separate and dry the EtOAc layer over sodium sulfate. Filter and concentrate in vacuo. Redissolve the resulting residue in a minimal amount of EtOAc and pass through a pad of silica to afford 0.248 g (83%) of the title compound. mp: 169-171° C.; MS (ES): m/z 452 (M+1), HPLC: Rt=2.2 min (89%).

Provenance & Evidence