Toluene → HCID 46178372, compound

Participants

Reaction Conditions

Reaction Steps

To 127 mg (0.317 mmol) of methyl 4-((2S,3S)-5-(2-(dimethylamino)ethyl)-3-hydroxy-4-oxo-2,3,4,5-tetrahydrobenzo[b][1,4]thiazepin-2-yl)benzoate in 160 μL of pyridine at 0° C. was added 25 μL (0.35 mmol) of acetyl chloride. The solution was stirred at 0° C. for 2 hours. The solvent was evaporated to leave a residue which was co-evaporated with toluene (3×). The material was then dissolved in DCM, washed with 1 N NaOH, dried (Na2SO4), and evaporated. Purification was afforded by flash chromatography on silica gel, eluting first with DCM then gradually increasing to 5% methanol/DCM to give 1m. MS found M+H=443. The observed 1H NMR coupling constants between the C2 and C3 methine protons (J=7.4 Hz) confirmed retention of the cis stereochemical relationship. The hydrochloride salt of 1m was recrystallized from isopropanol/ether; mp 214-216° C.; [α]25D+98.9° (c 0.99, CHCl3).

Provenance & Evidence