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27th March 2012 @ 01:48
SM recovered.

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Synthesis of an oxazole linked aryl pyrrole ester from PMY 42-1 and ethyl bromopyruvate. Intermediate in synthesis of ester isostere of TCMDC-123812 PMY 10-6

PMY45-1.png

Reaction Start Time: 15.50 27/03/12
PMY 42-1 (80 mg, 0.34 mmol, 1 equiv.) and dried NaHCO3 (145 mg, 1.72 mmol, 5.0 equiv.) were stirred in dry THF (8 mL) at room temperature. Ethyl bromopyruvate (52 μL, 0.41 mmol, 1.2 equiv.) was added and the reaction heated to 57 °C. After 18 hours, reaction showed mostly SM by TLC. A further portion of ethyl bromopyruvate (26 &muL;, 0.20 mmol, 0.6 equiv.) was added and the reaction refluxed for 3 hours and then cooled. The mixture was filtered through celite then concentrated under high vacuum to a brown oil (84 mg). 1H NMR mainly SM. Mass spec is inconclusive.

Mass Spec:
ESI mass spec


NMR:
1H NMR crude


Reference:
doi:10.1021/jo048106q
doi:10.1021/jo702305g

See also:
Synthesis of pyrrole amide (PMY 42-1)
Discussion on The Synaptic Leap.

Risk and Hazard Assessment:
RA


InChi:

Starting Material: InChI=1S/C13H13FN2O/c1-8-7-12(13(15)17)9(2)16(8)11-5-3-10(14)4-6-11/h3-7H,1-2H3,(H2,15,17)
Product: InChI=1S/C18H17FN2O3/c1-4-23-18(22)16-10-24-17(20-16)15-9-11(2)21(12(15)3)14-7-5-13(19)6-8-14/h5-10H,4H2,1-3H3
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Attached Files
Scheme
RA
ESI mass spec
1H NMR crude
Comments
Re: Synthesis of aryl pyrrole oxazole ester (PMY 45-1) by OSDD Malaria
25th January 2014 @ 02:02
Related to methyl ester OSM-S-62