Sodium Hydroxide → HCID 21896699, compound

Participants

Reaction Steps

To a solution of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-bromo-8-ethoxycarbonylmethoxy-2,3,4,5-tetrahydro-1,2,5-benzothiadiazepine (Method 1; 0.184 g, 3.24*10−4 mol) in EtOH (7 ml) was added NaOH (0.052 g, 1.30 mmol) and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc and 0.5 M HCl. The aqueous layer was extracted twice more with EtOAc and the combined organic extracts were washed with brine and concentrated. The crude product was purified by preparative HPLC using an MeCN/ammonium acetate buffer as eluent and freeze-dried to give the title compound in 0.173 g (99%) as a white solid. NMR (400 MHz, CD3OD) 0.70–0.85 (m, 6H), 0.95–1.70 (m, 12H), 3.90 (brs, 2H), 4.50 (s, 2H), 6.90–7.40 (m, 7H).

Provenance & Evidence