Sodium Iodide → HCID 131725712, compound

Participants

Reaction Steps

A suspension of (13) (1.0 g, 4.2 mmol) and NaI (0.755 g, 5.04 mmol) in acetone (15 mL) was stirred for 1 hour at room temperature, followed by addition of a solution of (1) (0.595 g, 3.5 mmol) and CaCO3 (1.738 g, 17.4 mmol) in DMF (15 mL). The mixture was stirred at room temperature overnight, followed by filtration. The filtrate was concentrated in vacuo and the residue dissolved in EtOAc (100 mL), washed with water (100 mL), brine (100 mL), and dried over anhydrous MgSO4. The solvent was removed in vacuo and the residue purified by silica gel column chromatography (0 to 5% MeOH in CHCl3, v/v) to give 340 mg (28.6%) of product (14): 13C NMR (CDCl3+CD3OD) δ 28.429 (3×CH3 of Boc), 34.868 (CH2C(═O)O), 36.109 (NHCH2CH2), 61.223 (OCH2S), 81.537 (C(CH3)3), 142.901 (Ar—C), 145.640 (Ar—C), 148.623 (Ar—C), 149.749 (Ar—C), 152.181 (Ar—C), 156.738 (NHC(═O)O), 172.431 (C(═O)O).

Provenance & Evidence