Triethylamine → HCID 68510661, compound

Participants

Reaction Steps

To a 0° C. solution of compound 49 (170 mg, 0.48 mmol) in dry CH2Cl2 (5 mL) were added methanesulfonyl chloride (78 μL) followed by dropwise addition of Et3N (0.13 mL). The reaction was stirred for 2.5 h under N2 at room temperature. The reaction mixture was diluted with CH2Cl2 (40 mL), washed with 1N HCl (10 mL), water (2×10 mL), and saturated NaCl (2×10 mL). Dried over MgSO4 and filtered. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 4:1) to afford a mixture of mono and bis-sulfonamides (215 mg). To a solution of the mixture of mono and bis-sulfonamides (200 mg) in 3 mL of MeOH and THF (2:1) was added NaOH (38 mg in 0.1 mL of H2O). The reaction was stirred for 45 min. at room temperature. Most of the solvent was evaporated under vacuum, the residue was dissolved in water (15 mL), and extracted with EtOAc. The combined organics were dried over MgSO4 and filtered. The solvent was removed under reduced pressure, and the product was purified by column chromatography (EtOAc/hexanes 2:1) to afford 53 as a white solid (120 mg); MS m/z: 434 (M+H)+. Anal. Calcd. For, C19H19N3O3S3.0.1H2O: C, 52.39; H, 4.86; N, 9.65; S, 22.08. Found: 52.06; H, 4.57; N, 9.45; S, 21.80.

Provenance & Evidence