Ethyl bromoacetate → HCID 18442431, compound

Participants

Reaction Steps

Ethyl bromoacetate (0.101 g, 0.604 mmol) was added to a mixture of 1,1-dioxo-3,3-dibutyl-5-(4-chlorophenyl)-7-methylthio-8-hydroxy-2,3,4,5-tetrahydro-1,5-benzothiazepine (Method 99; 0.194 g, 0.402 mmol), anhydrous Na2CO3 (0.192 g, 1.81 mmol) and tetrabutylammonium bromide in MeCN (5 ml). The reaction mixture was refluxed for 3.5 hours. The solvent was evaporated under reduced pressure and the residue was extracted with DCM/water. The organic layer was separated, dried and evaporated under reduced pressure. The crude product was purified by column chromatography using DCM/EtOAc (100:5 and 100:10) as eluent to give the title compound 0.197 g (86%). NMR (300 MHz) 0.80–0.89 (m, 6H), 1.0–1.45 (m, 15H), 2.34 (s, 3H), 3.16 (s, 2H), 3.68 (s, 2H), 4.30 (q, 2H), 4.71 (s, 2H), 7.05–7.11 (m, 3H), 7.19 (s, 1H), 7.29–7.35 (m, 2H).

Provenance & Evidence