反应详情

N-Acetyl-penicillamine (3.0 mg, 0.0154 mmol, racemic) and DIEA (7 μL, 0.04 mmol) were dissolved in DMSO (223 μL) and then transferred to a solution of 2-bromo-N-[3′-(5-carbamimidoyl-2-methylsulfanyl-thiophene-3-sulfonyl)-6-methyl-biphenyl-2-yl]-acetamide trifluoroacetate (20 mM in DMSO, 230 μL, 0.0046 mmol, prepared from the title compound described in Example 249). The reaction was mixed on a shaker for 1 h at rt. Bromomethyl wang resin (16 mg, 1.47 mmol/gm) was added to scavenge the excess thiol. After 2 h of shaking, the resin was filtered and the filtrate was directly purified using RP-HPLC as previously described in Example 246, step b, to afford 1.5 mg (50%, single peak on analytical RP-HPLC) of the title compound as a glassy solid. ESI-MS (m/z): Calcd. for C28H32N4O6S4: 649.1 (M+H); found: 649.1.