Compound ML302F

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InChIKey ZCOCHUAGSBNGCP-CLTKARDFSA-N

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Compound ML302 (240 mg, 0.5 mmol) was dissolved in 1M NaOH (4 mL) upon which a colour change to deep red was observed. The clear reaction mixture was warmed to 60 °C and stirred for 45 min (reaction colour changes from deep red to yellow) afterwards consumption of starting material was observed. The reaction mixture was cooled to r.t. and subsequently carefully acidified with 1M HCl (5 mL). A white precipitate was formed and collected by centrifugation (4000g/10 min). After removal of the liquid phase the white solid was resuspended in H₂O (2 mL) and again collected through centrifugation. This process was repeated twice more. The obtained solid was dried under high vacuum overnight. The product was obtained as an inseparable mixture of E/Z isomers in a 1:4 ratio as an off-white solid (40 mg, 28%). TLC (CH₂Cl₂/MeOH 4:1) R_f = 0.67. ¹H NMR (400 MHz, CDCl₃) δ (assigned for the major isomer) = 7.69 (s, 1H), 7.45 (dd, J = 8.5, 1.0 Hz, 1H), 7.33 - 7.37 (m, 1H), 3.89 (br. s., 1H) ppm. ¹³C-NMR (200 MHz, CDCl₃) δ = 168.1, 134.7, 132.8, 132.4, 132.1, 132.1, 130.7, 130.6, 128.7 ppm. LRMS m/z calcd. for C₉H₄Cl₃O₂S [M-H] = 280.90, found [M-H] =280.8.