Tris(hydroxymethyl)aminomethane → methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}{[(E)-2-phenylvinyl]-sulfonyl}amino)methyl]phenoxy}acetate

Participants

Reaction Steps

A solution of methyl {4-[({4-[(4-butylphenyl)ethynyl]benzyl}amino)methyl]phenoxy}-acetate (42 mg, 0.10 mmol) and β-styrene sulfonyl chloride (Aldrich, 23 mg, 0.11 mmol) in DCM (2 mL) was stirred at rt overnight in presence of a morpholine resin (1.5 eq., Novabiochem HL, 3.8 mmol/g) (1.5 eq). Trisamine resin (1 eq, Novabiochem, 3.5 mmol/g) was then added and the mixture stirred at rt for an additional 2 hrs. The reaction mixture was then filtrated and the solvent was removed under reduced pressure to give 55 mg (95%) of the title compound. HPLC, Rt: 5.8 min (purity: 83%). M+(ESI): 608.2.

Provenance & Evidence