Chlorosuccinimide → HCID 131729375, compound

Participants

Reaction Steps

A solution of (3aR,7S,7aS)-7-(4-amino-3-fluoro-benzyl)-3-(3-tert-butyl-benzyl)-5,5-dioxo-hexahydro-1-oxa-5lambda*6*-thia-3-aza-inden-2-one (4.0 g, 8.69 mmol, example 81) and N-chlorosuccinimide (1.276 g, 9.55 mmol) in ACN (130 mL) was heated at reflux for 2 h. The reaction mixture was evaporated and the residue was purified by chromatography (Combi Flash, 120 g silicagel, hexane-EtOAc) to provide the title compound as a colorless solid: TLC (toluene-EtOAc 3:1) Rf=0.42; UPLC RtD=1.887 min; [M+NH4]+=512, 514; 1H NMR (600 MHz, DMSO-d6): δ 7.38 (s, 1H), 7.32 (d, 1H), 7.27 (t, 1H), 7.13 (d, 1H), 6.93 (s, 1H), 6.89 (d, 1H), 5.28 (s, 2H), 4.42 (d, 1H), 4.21 (d, 1H), 4.11 (t, 1H), 3.68 (m, 2H), 3.46 (t, 1H), 3.05 (m, 2H), 2.78 (d, 1H), 2.50 (m, 2H), 1.26 (s, 9H).

Provenance & Evidence