Methanol → N-(tert-Butyl)-1H-pyrrole-3-sulfonamide

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Water	HCID 962	—
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	N-(tert-Butyl)-1-tosyl-1H-pyrrole-3-sulfonamide	HCID 86719139	—
Solvent	Acetic Acid	HCID 176	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-(tert-Butyl)-1H-pyrrole-3-sulfonamide	HCID 19693846	69%

Reaction Conditions

Temperature	60 °C

Reaction Steps

To a solution of compound 27c (665 mg, 1.87 mmol) in a mixture of THF (12 mL), MeOH (12 mL) and water (3 mL) was added K2CO3 (3.1 g, 22 mmol) and then the solution was heated at 60° C. overnight, cooled, acidified to pH=5 with AcOH and extracted with EA twice. The combined organic layers were washed with water (3×) and brine, concentrated and purified by CC (PE/EA=2/1) to give compound 27d (260 mg, 69%) as a solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08946446B2
Source dataset	uspto-grants-2015_02
ORD ID	ord-23659cd8d00544bf89aaaa18cadb6b73
Source note	uspto-grants-2015_02