Water → HCID 67906924, compound

Participants

Reaction Steps

A solution of trans-2-[3-(2-hydroxy-n-propylsulfonyl)-4-n-propoxy-5-(2-bromoethoxy)phenyl]-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran (47 mg, 0.07 mmol)(Example 19A) in DMF (250 mL) was added to a mixture of 2-mercaptoimidazole (25 mg, 0.25 mmol) and NaH (56%; 10 mg, 0.25 mmol) in DMF (0.5 mL) under nitrogen, and the mixture was stirred at room temperature for 30 min. Water (5 mL) and ethyl ether (5 mL) were added, and the mixture was stirred for another 5 min. The ethereal layer was separated, dried over MgSO4, and filtered. The filtrate was evaporated to a residue, which was purified by preparative TLC (EtOAc) to give the title compound: Rf 0.5; MS, m/z 636 M+. ; NMR (CDCl3) δ 1.02 (t, CH2CH2CH3), 1.24 (d, CH2CHOHCH3), 1.85 (m, CH2CH2CH3), 2.0 and 2.49 (2 m, H-3 and H-4), 3.42 (m, CH2S), 3.54 (m, CH2CHOH) 3.84 and 3.88 (2 s, 3 OCH3), 4.18 (m, CH2CH2S), 4.3 (m, CH2CHOH), 4.38 (t, CH2CH2CH3), 5.22 (m, H-2 and H-5), 6.62 (s, C5ArH), 6.96 (s, NH), 7.1 (s, imidazole), 7.32 and 7.50 (2 d, J=1.5 Hz, C2ArH).

Provenance & Evidence