Ethyl N-(4-methylphenyl)sulfonylcarbamate

Uses

Tosylurethane (Gliclazide EP Impurity C) is an intermediate in the synthesis of Gliclazide (G409877), a sulfonylurea hypoglycemic agent. Used as an antidiabetic.

Synthesis

GENERAL STEPS: Dissolve 4-methylphenylsulfonylcarbamate (Compound, CAS:31224-37-0) in selected alcohol (ethanol, 2 mL) in a microwaveable reaction vial. The reaction vial was sealed using an aluminum cap with a PTFE-faced septum. The reaction mixture was placed in a microwave reactor and radiantly heated at 100-120°C for 20-60 min. Upon completion of the reaction, the crude product was concentrated under reduced pressure and the residue was subsequently purified by silica gel column chromatography to finally obtain the target product, ethyl N-(4-methylphenyl)sulfonylcarbamate.

References

[1] Tetrahedron Letters, 2016, vol. 57, # 13, p. 1476 - 1478