2-Morpholinoethanol → HCID 72192066, compound

Participants

Reaction Conditions

Reaction Steps

N-(2,4-dimethylphenyl)-3-hydroxy-N-isobutylbenzenesulfonamide (76.9 mg, 0.231 mmol), 2-morpholinoethanol (0.035 mL, 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 vessel. Tetrahydrofuran (THF) (4 mL) was added followed by diisopropyl diazene-1,2-dicarboxylate (DIAD) (0.056 ml, 58.3 mg 0.288 mmol). The reaction vial was sealed and left to stir overnight at 20° C. 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 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 (pre-conditioned with 1 mL DMF, followed by 6 mL MeOH:H2O (5:1)). The semi-purified material was eluted with 6 mL MeOH:H2O (5:1). This was concentrated and dissolved in 1:1 MeOH:DMSO (1 mL) then further purified by mass directed autoprep (formic acid modifier). The relevant fractions were concentrated under a stream of nitrogen to give the required product, 17 mg. LCMS [LCMS1] Rt 1.03 min, m/z (ES+) 447 (M+H).

Provenance & Evidence