1-Hydroxybenzotriazole → tert-Butyl 2-(methoxy(methyl)amino)-1-methyl-2-oxoethylcarbamate

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Reaction Steps

2-t-butoxycarbonylamino-propionic acid (25 g, 132 mmole) was dissolved in dimethylformamide (DMF, 300 ml). N,O-dimethylhydroxylamine HCl (12.9 g, 132 mmol) was added, followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide HCl (26.6 g, 139.0 mmol), HOBT (17.8 g, 132 mmol), and NaHCO3 (44.4 g, 528 mmol). The reaction mixture was stirred under nitrogen for 48 h. The solution was then filtered, and the solvent evaporated under reduced pressure. The residue was dissolved in CH2Cl2 and washed with 2% aqueous HCl, saturated aqueous NaHCO3, and water. The organic layers were dried over sodium sulfate and evaporated under reduced pressure to provide [1-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester (intermediate XIIIa, 12.84 g, 42%). M+=233.

Provenance & Evidence