Sulfuryl chloride → HCID 21700739, compound

Participants

Reaction Steps

The appropriate sulfonyl chloride (1.5 equivalents, 0.18 mmol) and 70 mg of a morpholino-resin (prepared according to Booth and Hodges, Supra., 1997) were mixed in 1 mL dichloromethane in each of 10 different vials. One milliliter of a 0.12 M stock solution of 6-amino-2-(dibenzofuran-2-sulfonylamino)-hexanoic acid methyl ester hydrobromide in triethylamine was added to each of the vials. The vials were sealed and shaken for 16 hours at room temperature. An excess of an amino-resin and an isocyanato-resin (also both prepared according to Booth and Hodges, Supra, 1997) was added to each vial and shaken for 16 hours to quench unreacted starting materials. Each reaction was filtered through a plug of glass wool, and the resins were washed with 2 mL tetrahydrofuran. The filtrate was evaporated under a stream of nitrogen, and the residue in each vial was redissolved in 1 mL dioxane. One milliliter of a 0.6 M aqueous solution of lithium hydroxide was added, and the resulting mixtures were shaken for 16 hours. Each reaction was washed with diethyl ether, and the aqueous layer was then acidified with 1 molar hydrochloric acid. The reactions were extracted with ethyl acetate and evaporated under a stream of nitrogen to leave the expected products. The compounds were analyzed by LC/MS to determine purity and presence of expected molecular ion.

Provenance & Evidence