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30th January 2013 @ 14:35

 

Crude pt-6-4 (68.3 mg, 131 umol) was dissolved in MeOH (20 ml) and to this was added concentrated aqueous ammonia (10 ml). The resulting suspension was stirred vigorously overnight, when TLC and mass spec (PT-1-5RM, ESI+, [M+Na]+ = 512) indicated complete conversion to desired product. The solvents were removed in vacuo; 1H NMR (PT-1-5A) indicated complete conversion to the primary amide, with impurities. The product was purified by vacuum filtration through a plug of SiO2 (15-40 um) in a pasteur pippette (0-10% MeOH/CHCl3) to give the title compound as a tan foam (PT-1-5B, 30.1 mg, 61 umol, 46%) which still contained some impurities. The product was purified by dry column vacuum chromatography (50-100% ethyl acetate/heptane, then 0-5% methanol in ethyl acetate) to give the title compound as a tan oil (16.8 mg, 35 umol, 26%).

 

Analysis: 1H and 13C NMR consistent with title compound plus traces of residual solvent. Mass spec consistent (observed: M+Na, 512). Note: samples submitted under incorrect sample code (112b1) due to operator error.

 

ESI-Acc (Finnegan MAT-900 ESI-Positive HRMS): Expected 489.11466 (C13H24O6FS2) found 489.11439 (0.26 ppm)

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Attached Files
PT-1-5 scheme.png
PT-1-5-RM mass spec.jpg
PT-1-5A.pdf
Pt-1-5-C1 13C.pdf
Pt-1-5-C1 1H.pdf
ThomsonPatrick_ptm112C1_290313_1H-13C_av500.tar