Reaktion #57551

Reaktionsgleichung

N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-L-valine t-butyl ester

→

N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)glycine

Ausbeute 73.1%

Lösungsmittel

—

solution

TFA

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solvent was removed under vacuum
2. 2
   SonstigeThe crude product was triturated with hexane/ethyl acetate (95:5) three times

Vorschrift

N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)-L-valine t-butyl ester (60 mg) was dissolved in a 95% solution of TFA in methylene chloride (5 mL). The solution was stirred at room temperature for 4 h and the solvent was removed under vacuum. The crude product was triturated with hexane/ethyl acetate (95:5) three times. The product was lyophilized with benzene to give 36 mg of N-({4′-[(1-benzofuran-2-ylcarbonyl)amino]-1,1′-biphenyl-4-yl}sulfonyl)glycine. LCMS MH+ (m/z) 493. 1H NMR (300 MHz, DMSO-d6): δ 10.53 ppm (s, 1H), 7.81-7.54 ppm (m, 11H), 7.34 ppm (dd, 1H, J1=8.4 Hz, J2=8.4 Hz), 7.20 ppm (dd, 1H, J1=8.4 Hz, J2=8.4 Hz), 3.35 ppm (d, 1H J=6.0 Hz), 1.79 ppm (m, 1H), 0.63 ppm (dd, 6H, J1=13.8 Hz, J2=6.6 Hz).

Quelle