Structure−Activity Studies on Anticonvulsant Sugar ... - ACS Publications

Bruce E. Maryanoff*, Michael J. Costanzo, Samuel O. Nortey, Michael N. Greco, Richard P. Shank, James J. Schupsky, Marta P. Ortegon, and Jeffry L. Vau...
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J. Med. Chem. 2003, 46, 652

Additions and Corrections 1998, Volume 41 Bruce E. Maryanoff,* Michael J. Costanzo, Samuel O. Nortey, Michael N. Greco, Richard P. Shank, James J. Schupsky, Marta P. Ortegon, and Jeffry L. Vaught: Structure-Activity Studies on Anticonvulsant Sugar Sulfamates Related to Topiramate. Enhanced Potency with Cyclic Sulfate Derivatives. Page 1329. The procedure for the synthesis of 6 should read “...concentrated in vacuo to a syrup, which was dissolved in toluene and concentrated to a solid. The solid was triturated with hexanes and dried in vacuo to give 6 (1.20 g, 11%) as a colorless powder: mp 5052 °C; ...”. Chromatography was not performed. The 1H NMR resonance at δ 2.40 should read “δ 3.40”. The molecular formula should have “C12” instead of C11; the “0.1C7H8” represents residual toluene. The corresponding information on 6 in Table 1 (p 1317) should be corrected: % yield should read “11%” and “LC” should be deleted. Page 1330. To the procedure for the synthesis of 8, “and concentrated to a solid” should be added to the end of the phrase “ ... treated with acetic acid (3.32 g), stirred for 5 min,”. Page 1331. In the synthesis of 32, the 10.0 g of intermediate 39 represents “0.029 mol”. Page 1332. The 1H NMR resonance “3.75-4.05 (m, 2H, H6)” for 32 should be deleted, as it is redundant. Page 1333. The procedure for the synthesis of 47 is missing some operations. It should read “... at 23 °C for 5 days and poured into ice-water (225 mL). The organic phase was separated, and the aqueous phase was washed with chloroform (3 × 75 mL). The combined organic solution was washed sequentially with NaHCO3 (saturated aqueous) and brine, and then it was dried (MgSO4) and concentrated in vacuo. The residue was dissolved in methanol (180 mL), treated with NaHCO3 (20.2 g, 0.24 mmol), and stirred for 16 h. After filtration, the solution was concentrated in vacuo to a yellow solid, which was partitioned between chloroform and water. The chloroform solution was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified...”. JM020527H 10.1021/jm020527h Published on Web 01/18/2003