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14th February 2012 @ 06:07
Target synthesised in 34% yield. 05/03/12 Purified further by trituration (Et2O) to obtain the pure product as a white powder (28 mg). === Synthesis of TCMDC-123794 using the method used for [url=]MY 31-5[/url] and [url=]PMY 34-1[/url] for the preparation of the acid chloride. Acid chloride batch [url=]JRC 3-1[/url]. [b]Reaction start time: 17.30 14/02/12[/b] [url=]PMY 9-1[/url] (100 mg, approx 0.38 mmol, approx 1.2 equiv. Contains slight impurity) and DIPEA (0.16 mL, 1.22 mmol, 2.3 equiv.) were stirred in dry THF (2 mL). A solution of acid chloride [url=]JRC 3-1[/url] (80 mg, 0.32 mmol, 1 equiv.) in THF (3 mL) was added to the mixture and the reaction heated to 80 °C. After 17 hours, TLC shows new products and SM. 4-DMAP (approx. 20 mg, 0.16 mmol, 0.5 equiv.) added. After a further one hour, reaction still shows SM by TLC. Cooled to room temperature and concentrated under reduced pressure. Residues (orange oily solid) purified by chromatography (45% EtOAc/hexane, then 2% MeOH/DCM) gave impure product (80 mg) as a yellow solid. Further chromatography (55-100% EtOAc/hexane) gave the product (52 mg, 34%) as a off-white crystals. Mostly pure by 1H NMR. [b]TLC (10% MeOH/DCM) visualised with UV and vanillin:[/b] [data]1588[/data] left plate, 17 hours. Right plate, 18 hours. [b]NMR:[/b] [data]1592[/data][data]1880[/data][data]1878[/data][data]1876[/data] [b]Mass Spec:[/b] [data]2184[/data] [b]See also:[/b] [blog]1905[/blog] [blog]1819[/blog] [blog]541[/blog] [blog]1009[/blog] [blog]1009[/blog] [b]Risk and Hazard Assessment:[/b] See: [blog]499[/blog]
Attached Files
TLC 17 hours
1H NMR after 1st column
1H NMR after 2st column
1H NMR triturated
1H NMR triturated impurities
ESI mass spec