Compound 8
aminal
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
General procedure for the preparative synthesis of aminals (8): 2-Aminothiazole (7; 0.5 g, 5.0 mmol) was added to a solution of 2 (2.5 mmol, 0.5M) in sodium phosphate buffer (1M, pH 7, 5 mL), and vigorously stirred for 24 h at room temperature. The resultant suspension was centrifuged and the supernatant removed. The precipitate was washed with ice-cooled water (3 × 5 mL). The isolated precipitate was dried to yield aminal 8 as a solid in all cases.
General procedures for the reaction of 2-aminothiazole (7) with aldehydes/ketones (2): 2-aminothiazole (7; 0.1 g, 1.0 mmol) was added to a stirred solution of 2 (0.5 mmol, 0.5M) in sodium phosphate buffer (1M, pH 7, 1 mL) at room temperature. After 24 h the reaction mixture was diluted with DMSO (5 mL), an aliquot (100 µL) was further diluted with DMSO-d6 (0.6 mL) and NMR spectra were acquired. The formation of aminal 8 was quantified using 1,3,5-trimethoxybenzene as an internal standard (Supplementary Table 12).
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