Hydrochloric Acid → N-(4-(4-(ethyl(4,4-dimethylpentanoyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide

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Reaction Steps

A stirred solution of 4,4-dimethylpentanoic acid (2.07 g, 0.0159 mol) and triethylamine (2.28 ml, 0.0163 mol) in THF (120 ml) was cooled to -8° C. and treated dropwise with isobutyl chloroformate (2.12 ml, 0.0163 mol). The mixture was kept at -8° C. for 1.5 hour and treated with a mixture of the product from Example 7 Step II (4.0 g, 0.014 mol), triethylamine (2.28 ml, 0.0163 mol) and THF (160 ml). This mixture was kept at -8° C. for 1.5 hour and then treated slowly with 1N HCl (158 ml) and extracted with EtOAc. The extract was washed with water, dilute NaHCO3 and water, dried (MgSO4) and concentrated to give 4.4 g of N-(4-(4-(ethyl(4,4-dimethylpentanoyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide. The mass spectrum had m/z 398 (M+).

Provenance & Evidence