Triethylamine → HCID 57979827, compound

Participants

Reaction Conditions

Reaction Steps

N-(tert-Butoxycarbonyl)-N,O-dimethyl-L-serine (1.5 g, 6.43 mmol) and triethylamine (0.99 ml, 7.07 mmol) in tetrahydrofuran (20 ml) were cooled to −15 to −17° C. Ethyl chloroformate (0.68 ml, 7.07 mmol) was added drop wise followed by concentrated ammonium hydroxide (12 ml). The mixture was stirred at 0 to 5° C. for 2 hours. Saturated ammonium chloride solution was added and the layers separated. The aqueous layer was re-extracted with ethyl acetate and the combined organics dried (MgSO4) and concentrated under reduced pressure. The residues were dissolved in dioxane (10 ml) and 4M hydrogen chloride in dioxane (10 ml) was added and the mixture stirred for 1 hour. The mixture was evaporated and the residue dissolved in methanol, absorbed onto an SCX column, washed with methanol and eluted with 7N ammonia in methanol. Appropriate fractions were combined and evaporated to give N2,O-dimethyl-L-serinamide (576 mg, 68%) as a white, crystalline solid; 1H NMR spectrum: (DMSO d6) 1.92 (brs, 1H); 2.21 (s, 3H); 2.98 (t, 1H); 3.21 (s, 3H); 3.37 (m, 2H); 7.07 (brs, 1H); 7.30 (brs, 1H).

Provenance & Evidence