[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:12]([CH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20](OCC)=[O:21])[N:19]=1)[CH3:13])(OCC)=O.[O-]S([O-])(=O)=O.[Na+].[Na+].[OH-].[K+]>O1CCCC1>[CH3:13][N:12]([CH2:14][C:15]1[S:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=1)[CH3:7]To a cooled suspension of lithium aluminum hydride (8.4 g; 0.22 mole) in 80 ml of dry tetrahydrofuran was added a solution of 2-(N-carbethoxy-N-methylamino)methyl-4-carbethoxythiazole (20.0 g; 0.07 mole) [prepared in Step C] in 160 ml of dry tetrahydrofuran over a 1 hour period. The reaction mixture was heated at reflux temperature for 8 hours, then cooled and decomposed with Na2SO4 and 40% aqueous potassium hydroxide. The mixture was filtered, dried and evaporated under reduced pressure to give 4.2 g of the title compound as an oil; TLC (aluminum oxide/CH3CN) gave RF=0.45. The NMR spectrum (60 MHz) in CDCl3 gave the following resonances δ: 7.17 (s, 1H); 4.73 (d, 2H); 3.43 (s, 2H); 3.35 (s, 6H).
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