Methanesulfonyl chloride → HCID 13561105, compound

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Reaction Steps

The amine from Step IV (1.7 g, 0.00585 mol) is mixed with 4.6 ml of pyridine under nitrogen, the mixture cooled in an ice bath and treated dropwise, over 5 min, with 0.5 ml (0.74 g, 0.0064 mol) of methanesulfonyl chloride. The mixture is stirred in the cold for 1 hr and at room temperature overnight. The solvent is removed in vacuo as an azetrope with toluene. The residue is taken up in CH2Cl2 (75 ml), washed with 25 ml of 8% NaHCO3 and the aqueous wash extracted with CH2Cl2 (2×75 ml). The organic pool is washed with brine, dried (Na2SO4) and concentrated to give a dark oil. This material is chromatographed over 500 ml of silica gel (eluted with 0.4% NH4OH-8% MeOH--CH2Cl2); 45 ml fractions are collected. The resulting material is further treated with cold, dilute NaOH to pH 12 and extracted with EtOAc (1×40 ml). The organic extract is washed with cold, dilute NaOH (2×5 ml) and the pooled aqueous wash extracted with EtOAc (2×25 ml) (each extract is washed with 5 ml of H2O). The pooled EtOAc extract is dried (Na2SO4) and concentrated in vacuo to give the title compound. The title compound is chromatographed over 50 ml of silica gel (eluted with 0.25% NH4OH-10% MeOH--CH2Cl2) and 20 ml fractions collected. Theory for C20H37N2O2S 369.2576; measured, 369.2576 by high resolution FAB MS. ##STR1##

Provenance & Evidence