1-Amino-3-methylpyrrole-2,4-dicarboxylic acid dimethyl ester synthesis
- Product Name:1-Amino-3-methylpyrrole-2,4-dicarboxylic acid dimethyl ester
- CAS Number:310431-26-6
- Molecular formula:C9H12N2O4
- Molecular Weight:212.2
3780-42-5
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310431-26-6
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Yield:310431-26-6 80%
Reaction Conditions:
Stage #1: dimethyl 3-methyl-1H-pyrrole-2,4-dicarboxylatewith sodium hydride in N,N-dimethyl-formamide;mineral oil; for 1 h;Inert atmosphere;Green chemistry;
Stage #2: with chloroamine in diethyl ether;N,N-dimethyl-formamide;mineral oil; for 0.166667 h;Inert atmosphere;Green chemistry;
Steps:
(f) Dimethyl 1-amino-3-methyl-1H-pyrrole-2,4-dicarboxylate (4)
To a stirred solution of compound 3 (8.73 g, 44.3 mmol) in DMF (60 mL) was added NaH (60 % dispersion in mineral oil, 2.30 g, 57.5 mmol). After stirring for 1 h, anhydrous ethereal monochloroamine (340 mL) was added under nitrogen atmosphere. The reaction mixture was stirred for 10 min and then quenched with aqueous Na2S2O3 (100 g/L, 200 mL). The mixture was diluted with water. The organic layer was separated and washed with brine, dried over anhydrous Na2SO4, and filtered. The solvent was evaporated in vacuo, and the crude product was purified by column chromatography (3.5:1 hexanes/EtOAc) to afford 4 (7.55 g, 80 %) as a white solid. 1H NMR (CDCl3): δ 7.48 (s, 1H), 5.22 (br s, 2H), 3.88 (s, 3H), 3.79 (s, 3H), 2.56 (s, 3H).
References:
Wang, Min;Gao, Mingzhang;Zheng, Qi-Huang [Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,# 16,p. 3700 - 3705]
40318-15-8
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310431-26-6
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623-43-8
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$11.00/10g
310431-26-6
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