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29th March 2012 @ 06:55
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Synthesis of the aryl pyrrole oxazole methyl ester from the standard aldehyde and serine methyl ester.

PMY46-1.png

Reaction Start Time: 17.00 29/03/12
PMY 2-5 (200 mg, 0.92 mmol, 1 equiv.) and DL-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.

TLC (30% EtOAc/hexane) visualised with UV and vanillin:
TLC 16 hours


NMR:
1H NMR oil
1H NMR crystal


Mass Spec:
ESI mass spec


See also:
Synthesis of aryl pyrrole oxazole ester (PMY 45-1)
Preparation of 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde (PMY 2-5)

Reference:
doi:10.1021/ol101346w

Risk and Hazard Assessment:
RA
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Scheme
RA
TLC 16 hours
ESI mass spec
1H NMR crystal
1H NMR oil