After INK1197 mw the reaction completion, verified by TLC, the product was precipitated after the addition of cold distilled water. 2–3 mL aq. Na2CO3 was added to make basic pH of 9. The product was filtered off, washed with distilled water and recrystallized from methanol. Light brown amorphous solid; Yield: 79%; M.P. 84–86 °C; Molecular formula: C19H24ClNO3S; Molecular weight: 381; IR (KBr, ѵmax/cm−1): 3078 (Ar C H stretching), 1621 (Ar C C stretching), 1369 (S O stretching); 1H NMR (400 MHz, CDCl3, ppm): δ 7.76 (d, J = 8.8 Hz, 2H, H-2′ & H-6′), 7.60 (d, J = 2.0 Hz, 1H, H-6), 7.49 (d, J = 8.8 Hz, 2H, H-3′ & H-5′), 6.99 (dd, J = 8.8, 2.0 Hz, 1H, H-4), 6.64 (d, J = 8.8 Hz,

1H, H-3), 3.57 (s, 3H, CH3O-2), 3.60 (q, J = 7.2 Hz, 2H, H-1′’), 1.19 (s, 9H, (CH3)3C-4′), Doxorubicin manufacturer 0.99 (t, J = 7.2 Hz, 3H, H-2′’); EI-MS: m/z 383 [M + 2]+, 381 [M]+, 366 [M-CH3]+, 350 [M-OCH3]+, 317 [M-SO2]+, 197 [C10H13SO2]+, 156 [C7H7ClNO]+. Light grey amorphous solid; Yield: 81%; M.P. 118–120 °C; Molecular formula: C18H22ClNO3S; Molecular weight: 367; IR (KBr, ѵmax/cm−1): 3080 (Ar C H stretching), 1614 (Ar C C stretching), 1367 (S O stretching); 1H NMR (400 MHz, CDCl3, ppm): δ 7.35 (d, J = 2.8 Hz, 1H, H-6), 6.95 (dd, J = 8.8, 2.8 Hz, 1H, H-4), 6.79 (s, 2H, H-3′ & H-5′), 6.66 (d, J = 8.8 Hz, 1H, H-3), 3.76 (s, 3H, CH3O-2), 3.39 (q, J = 7.2 Hz, 2H, H-1′’), 2.57 (s, 6H, CH3-2′ & CH3-6′), 2.28 (s, 3H, CH3-4′), 0.99 (t, J = 7.2 Hz, 3H, H-2′’); EI-MS: m/z 369 [M + 2]+, 367 [M]+, 352 [M-CH3]+, 336 [M-OCH3]+,

303 [M-SO2]+, 183 [C9H11SO2]+, 156 [C7H7ClNO]+. Dark grey amorphous solid; Yield: 89%; M.P. 102–104 °C; Molecular formula: C16H18ClNO4S; Molecular weight: 355; IR (KBr, ѵmax/cm−1): 3056 (Ar C H stretching), 1603 (Ar C C stretching), 1369 (S O stretching); 1H NMR (400 MHz, CDCl3, ppm): δ 7.62 (d, J = 8.8 Hz, 4-Aminobutyrate aminotransferase 2H, H-2′ & H-6′), 7.18–7.22 (m, 2H, H-4 & H-6), 6.90 (d, J = 8.8 Hz, 2H, H-3′ & H-5′), 6.71 (d, J = 8.4 Hz, 1H, H-3), 3.84 (s, 3H, CH3O-4′), 3.56 (q, J = 7.2 Hz, 2H, H-1′’), 3.45 (s, 3H, CH3O-2), 1.02 (t, J = 7.2 Hz, 3H, H-2′’); EI-MS: m/z 357 [M + 2]+, 355 [M]+, 340 [M-CH3]+, 324 [M-OCH3]+, 291 [M-SO2]+, 171 [C7H7OSO2]+, 156 [C7H7ClNO]+. Blackish grey amorphous solid; Yield: 66%; M.P. 86–88 °C; Molecular formula: C17H19ClNO4S; Molecular weight: 367; IR (KBr, ѵmax/cm−1): 3084 (Ar C H stretching), 1607 (Ar C C stretching), 1351 (S O stretching), 1719 (C O stretching); 1H NMR (400 MHz, CDCl3, ppm): δ 7.99 (d, J = 8.0 Hz, 2H, H-2′ & H-6′), 7.78 (d, J = 8.0 Hz, 2H, H-3′ & H-5′), 7.48 (d, J = 2.4 Hz, 1H, H-6), 7.03 (dd, J = 8.0, 2.4 Hz, 1H, H-4), 6.71 (d, J = 8.0 Hz, 1H, H-3), 3.41 (s, 3H, CH3O-2), 3.30 (q, J = 7.2 Hz, 2H, H-1′’), 2.50 (s, 3H, CH3CO-4′), 1.00 (t, J = 7.