Water → tert-butyl 2-(4-amino-N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate

Participants

Reaction Conditions

Reaction Steps

Prepared using General Procedure 5. To a stirred solution of tert-butyl 2-(N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)-4-nitrobenzamido)acetate INT-68 (20 mg, 0.033 mmol) in THF (3 mL) and water (1 mL) was added sodium dithionite (17.2 mg, 0.099 mmol) and heated to 65° C. for 2 h. The reaction mixture was extracted with EA (10 mL) and washed with brine (10 mL). The organics were concentrated in vacuo to afford 13 mg (65%) of tert-butyl 2-(4-amino-N-(4-(5-(4-methylphenylsulfonamido)-1,2,4-oxadiazol-3-yl)benzyl)benzamido)acetate INT-69 as a white solid. LCMS-ESI (m/z) calculated for C29H31N5O6S: 577; found 576 [M−H]−, tR=2.41 min (Method 5).

Provenance & Evidence