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N-Succinimidyl N-Methylcarbamate is used as a reagent in the synthesis of Argifin, a natural product chitinase inhibitor with chemotherapeutic potential. N-Succinimidyl N-Methylcarbamate is also used as a reagent in the preparation of 5-Amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (A616300); a metabolite of Temozolomide (T017775) which is an imidazotetrazine alkylating agent and antineoplastic.

ChEBI: N-succinimidyl N-methylcarbamate is a member of the class of pyrrolidinones that is N-hydroxysuccinimide in which the hydroxyl hydrogen is replaced by a methylcarbamoyl group. It has a role as an apoptosis inducer. It is a carbamate ester, a dicarboximide, a pyrrolidinone and a N-hydroxysuccinimide ester. It is functionally related to a succinimide.

GENERAL STEPS: N-hydroxysuccinimide (5.83 g, 50.7 mmol) and ethyl acetate (20 mL) were added as solvents to a dry round-bottomed flask, and the mixture was cooled to 0 °C. Triethylamine (4.76 g) and methyl isocyanate (6.39 g, 0.112 mmol) were slowly added to the mixture at the same temperature. Subsequently, the reaction system was slowly warmed up to room temperature and stirred continuously at room temperature for 24 hours. Upon completion of the reaction, the volatiles were removed by distillation under reduced pressure. The crude product obtained was recrystallized with ethyl acetate/ether mixed solvent to afford the target compound N-succinimidyl-N-methylcarbamate (86% yield). The product was colorless needle-like crystals with a melting point of 148.0-149.0 °C (literature value: 148.0-152.0 °C).1H NMR (300 MHz, CDCl3) δ: 8.15 (1H, br, NH), 2.76 (4H, s, CH2CH2), 2.67 (3H, s, CH3); 13C NMR (22.5 MHz. CDCl3) δ: 170.66, 151.98, 27.98, 25.47; MS (FAB+) m/z: 173 (M + H).

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