Diisopropyl diazene-1,2-dicarboxylate → HCID 71543646, compound

Participants

Reaction Steps

N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide (76.9 mg, 0.231 mmol), (3,5-dimethylisoxazol-4-yl)methanol (36.7 mg, 0.288 mmol) and (4-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl)phenyl)diphenylphosphine (204 mg, 0.288 mmol) were added to a 2-5 mL Biotage microwave vessel. Tetrahydrofuran (THF) (4 mL) was added followed by diisopropyl diazene-1,2-dicarboxylate (DIAD) (0.056 mL, 0.288 mmol). The reaction vial was sealed and left to stir overnight at RT. The reaction mixture was concentrated in vacuo and then diluted with ethyl acetate (25 mL) and water (25 mL). The organic fraction was separated, dried and then concentrated in vacuo to give the crude product. The crude product was dissolved in DMF:H2O (9:1) 1 mL, and loaded onto a fluorous column (preconditioned with 1 mL DMF, followed by 6 mL MeOH:H2O (5:1). The semi purified fraction was eluted with 6 mL MeOH:H2O (5:1). The fraction was concentrated down, and dissolved in 1:1 MeOH:DMSO 1 mL and purified by mass directed autoPrep on Sunfire C18 column using Acetonitrile Water with a Formic acid modifier. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the required product, 37.7 mg.

Provenance & Evidence