4-Toluenesulfonyl chloride → tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate

Participants

Reaction Steps

Prepared using General Procedure 10. To a stirring solution of tert-butyl 2-(N-(4-(5-amino-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-67 (150 mg, 0.331 mmol) in THF (3 mL) was added potassium tert-butoxide (599 μL, 0.992 mmol) at room temperature. After 15 mins a solution of 4-methylbenzene-1-sulfonyl chloride (63.1 mg, 0.331 mmol) in THF (1 mL) was added. After 1 h the reaction mixture quenched with 1 M HCl (30 mL) and then extracted with EA (50 mL). The organic layer was concentrated in vacuo and purified by chromatography (EA/hexanes) to provide 20 mg (10%) of tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-68. LCMS-ESI (m/z) calculated for C29H29N5O8S: 607; found 608 [M+H]+, tR=2.50 min (Method 10).

Provenance & Evidence