Triethylamine → HCID 22464027, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold, stirred mixture of the product from Step 6 (6.03 g, 0.0117 mol) and triethylamine (4.55 ml) in methylene chloride (340 ml) is treated, portionwise during 10 min, with 3-nitrobenzenesulfonyl chloride (3.2 g) and kept in the ice bath for 15 min. It is then kept at ambient temperature for 16 h, diluted with CH2Cl2, washed with saturated NaHCO3 and brine, dried (MgSO4) and concentrated. A stirred solution of the residue (9.32 g) in a mixture of 2-propanol (250 ml), acetonitrile (250 ml), and concentrated ammonium hydroxide (250 ml) is warmed at 55° C. under a dry ice-acetone condenser for 3.5 h and kept at ambient temperature for 18 h. Additional ammonium hydroxide (50 ml) is added; the mixture is warmed at 55° C. for 30 min, kept at ambient temperature for 3 d and concentrated in vacuo. The aqueous residue is extracted with methylene chloride. The extract is washed water and brine, dried (Na2SO4) and concentrated to give 6.53 g of the titled product: 1H NMR (300 MHz, CDCl3) δ−0.11 (s, 3H), −0.06 (s, 3H), 0.76 (s, 9H), 3.03 (m, 3H), 3.24 (m, 1H), 3.79 (m, 2H), 4.02 (m, 2H), 4.52 (broad s, 1H), 4.65 (m, 1H), 5.27 (m, 2H), 7.08 (m, 1H), 7.38 (m, 5H), 7.62, 7.79 (broad s, 2H).

Provenance & Evidence