Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59229153, compound

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Reaction Steps

A flask containing 3-(tert-butoxycarbonyl)-2,2-dimethylthiazolidine-4-carboxylic acid (see Suaifan et al., Tetrahedron 62, 11245-11266 (2006); Kemp and Carey, J. Org. Chem. 54, 3640 (1989)) (4 g, 0.015 mol), HATU (7.3 g, 0.019 mol), HOAt (28 ml of 0.6M, 0.017 mol), N,O-dimethylhydroxylamine-HCl (2.92 g, 0.03 mol), diethylisopropylamine (5.1 L, 0.03 mol), and DMF (20 mL) was stirred at room temp for 17 h. Solvent was evaporated, and the residue was portioned between EtOAc (200 mL) and water (300 mL). The aqueous layer was extracted with EtOAc (50 mL), and the combined organic layers washed with 30% citric acid solution (2×100 mL), saturated bicarbonate (2×100 mL), and brine (1×50 mL). After evaporation, the crude residue was chromatographed on normal phase silica—eluting with heptane/EtOAc (2/1) to yield 3.84 g (84%) solid.

Provenance & Evidence