| Identification | More | [Name]
N-Succinimidyl-N-methylcarbamate | [CAS]
18342-66-0 | [Synonyms]
2,5-PYRROLIDINEDIONE, 1-[[(METHYLAMINO)CARBONYL]OXY]-
N-SUCCINIMDYL-N-METHYLCARBAMATE
N-SUCCINIMIDYL-N-METHYLCARBAMATE
N-Succinimidyl-N-methylcarbama
methyl isocyanate substitute
Methyl isocyanate substitute, MIC substitute | [Molecular Formula]
C6H7N2O4- | [MDL Number]
MFCD00800292 | [Molecular Weight]
171.13 | [MOL File]
18342-66-0.mol |
| Chemical Properties | Back Directory | [Melting point ]
148-153 °C | [density ]
1.41±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
Dichloromethane (Slightly), DMSO (Slightly) | [form ]
Solid | [pka]
11.00±0.46(Predicted) | [color ]
White to Off-White | [Water Solubility ]
Slightly soluble in water. | [Sensitive ]
Moisture Sensitive | [BRN ]
1531863 | [InChI]
InChI=1S/C6H8N2O4/c1-7-6(11)12-8-4(9)2-3-5(8)10/h2-3H2,1H3,(H,7,11) | [InChIKey]
XMNGSPOWUCNRMO-UHFFFAOYSA-N | [SMILES]
N1(OC(NC)=O)C(=O)CCC1=O | [CAS DataBase Reference]
18342-66-0(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [F ]
10-21 | [HS Code ]
2928.00.5000 |
| Hazard Information | Back Directory | [Uses]
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. | [Definition]
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. | [Synthesis]
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). | [References]
[1] European Journal of Medicinal Chemistry, 2014, vol. 82, p. 16 - 35
[2] Journal of Medicinal Chemistry, 1982, vol. 25, # 2, p. 178 - 182
[3] Journal of the American Chemical Society, 1995, vol. 117, # 4, p. 1240 - 1245 |
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