Ethyl bromoacetate → HCID 18442441, compound

Participants

Reaction Steps

To a suspension of 1,1-dioxo-3,3-dibutyl-5-phenyl-7-methylthio-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 3; 12.85 g, 28.71 mmol) in MeCN (150 ml) was added ethyl bromoacetate (3.85 ml, 34.6 mmol), tetrabutylammonium bromide (0.925 g, 2.869 mmol) and sodium carbonate (12.85 g, 121.2 mmol). The mixture was heated under reflux for 5 hours. The solvent was removed under reduced pressure and the residue was partitioned between DCM and 0.5 M HCl. The organic layer was washed with brine, dried (MgSO4) and concentrated. Chromatography using DCM/EtOAc (9:1) as eluent gave the desired product (15.45 g) as a tan oil. NMR 0.70–0.85 (m, 6H), 1.00–1.55 (m, 15H), 2.15 (s, 3H), 3.10 (s, 2H), 3.70 (brs, 2H), 4.25 (q, 2H), 4.70 (s, 2H), 6.65 (s, 1H), 6.90-7.30 (m, 6H).

Provenance & Evidence