CN(N=O)C(N[N+]([O-])=O)=N.[OH-].[K+].N#N.[C:15](=O)=O.CC(C)=O.[CH3:22][C:23]([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([CH2:27][C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)[C:24]([OH:26])=[O:25]>C(Cl)Cl.CCOCC>[CH3:15][O:25][C:24](=[O:26])[C:23]([CH3:22])([O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:27][C:28]1[S:29][CH:30]=[CH:31][CH:32]=1In a 100 mL beaker, 1.12 g of 1-methyl-3-nitro-1-nitrosoguanidine (MNNG) was added to a solution of ether (30 mL) and 5 N KOH (2.3 mL) and stirred until N2 evolution ceased. In another beaker, crude 2-methyl-2-phenoxy-3-thiophen-2-yl-propionic acid (1.00 g) was dissolved in CH2Cl2 (20 mL). The beaker containing the ether/base mixture was then placed in a Dewar flask containing dry ice/acetone, the aqueous layer was frozen and the ether layer decanted into the other beaker containing the crude acid solution. This mixture was then stirred for an additional 5 min, which by HPLC showed the reaction to be complete. The solvent was removed in vacuo to provide a crude oil. Purification by flash chromatography EtOAc:hexane (1:10) provided 533 mg of desired product (28%): 1H NMR (400 MHz, CDCl3) • 7.16-7.22 (m, 4 H), 6.96 (m, 1 H), 6.91 (m, 1 H), 6.84 (m, 2 H), 3.73 (s, 3 H), 3.49 (d, 1 H), 3.38 (d, 1 H), 1.42 (s, 3 H); MS (EI) 277.1 (M+H)+.
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