Thioglycolic Acid → [(6-Amino-9-benzyl-9H-purin-8-yl)thio]acetic acid

反応式

[C:1]([OH:5])(=[O:4])[CH2:2][SH:3].[H-].[Na+].Br[C:9]1[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:11]2[C:16]([N:17]=1)=[C:15]([NH2:18])[N:14]=[CH:13][N:12]=2>CN(C=O)C>[C:1]([CH2:2][S:3][C:9]1[N:10]([CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:11]2[C:16]([N:17]=1)=[C:15]([NH2:18])[N:14]=[CH:13][N:12]=2)([OH:5])=[O:4]

参加物

実験手順

A solution of thioglycolic acid (0.05 mL, 0.68 mmol) and NaH (0.05 g, 1.35 mmol, 60% in oil) in anhydrous DMF (3 mL) was stirred for 30 min at 0° C. under argon, then 23 (0.13 g, 0.45 mmol) in DMF (3 mL) was added. After stirring overnight at room temperature, the reaction mixture was concentrated to dryness, and the crude product was purified by reverse phase HPLC (5-50% ACN in TEAA over 20 min) to give 24 (0.07 g, 50%). Rt (0-10% A in B over 20 min.) 10.36 min.; 1H NMR (DMSO-d6) δ: 4.17 (s, 2H, SCH2), 5.31 (s, 2H, CH2), 7.10 (bs, 2H, NH2), 7.29 (m, 3H, H arom.), 7.35 (m, 2H, H arom.), 8.12 (s, 1H, H2); 13C NMR (DMSO-d6) δ: 34.91 (SCH2), 45.97 (CH2), 119.17 (C5), 127.77, 128.22 and 129.15 (CH), 136.63 (Cq), 147.77 (C8), 152.02 (C4), 152.51 (C2), 154.62 (C6); 169.85 (CO); HRMS (ESI-TOF) m/z calcd for [C14H13N5O2S+H]316.0868; found 316.0855.