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29th March 2012 @ 06:55
=== Synthesis of the aryl pyrrole oxazole methyl ester from the standard aldehyde and serine methyl ester. [b]Reaction Start Time: 17.00 29/03/12[/b] PMY 2-5 (200 mg, 0.92 mmol, 1 equiv.) and [size=8]DL[/size]-serine methyl ester hydrochloride (143 mg, 0.92 mmol, 1 equiv.) were stirred in THF (5 mL) with triethylamine (0.26 mL, 1.84 mmol, 1 equiv.) and MgSO4 (approx 200 mg). After 16 hours, the reaction was filtered. TLC shows mainly SM. Mixture concentrated under reduced pressure to an orange oil. Mass spec is inconclusive. [b]TLC (30% EtOAc/hexane) visualised with UV and vanillin:[/b] [data]2144[/data] [b]NMR:[/b] [data]3694[/data][data]3692[/data] [b]Mass Spec:[/b] [data]2180[/data] [b]See also:[/b] [blog]2789[/blog] [blog]2107[/blog] [b]Reference:[/b] doi:[url=http://dx.doi.org/10.1021/ol101346w]10.1021/ol101346w[/url] [b]Risk and Hazard Assessment:[/b] [data]2136[/data]
Attached Files
Scheme
RA
TLC 16 hours
ESI mass spec
1H NMR crystal
1H NMR oil