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Methyl 3-[[(2-methoxy-2-oxoethyl)amino]sulfonyl]-2-thiophenecarboxylate is an organic compound that is commonly used in the chemical industry.
This compound is synthesized through several synthetic routes, which differ in terms of the starting materials, reaction conditions, and the yield of the final product.
In this article, we will discuss the three most common synthetic routes for the preparation of Methyl 3-[[(2-methoxy-2-oxoethyl)amino]sulfonyl]-2-thiophenecarboxylate.
Route 1: via N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine
This route involves the synthesis of N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine, which is then reduced to Methyl 3-[[(2-methoxy-2-oxoethyl)amino]sulfonyl]-2-thiophenecarboxylate.
Step 1: Synthesis of N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine
To a solution of L-alanine (10 g, 85 mmol) in dichloromethane (50 mL), triethylamine (20 mL, 137 mmol) was added, and the reaction mixture was cooled to 0°C.
A solution of methyl iodide (6.
25 g, 46.
25 mmol) in dichloromethane (25 mL) was then added dropwise, and the reaction was stirred for 2 hours.
The reaction was then quenched with hydrochloric acid (2 mL), and the organic layer was separated and dried over anhydrous sodium sulfate.
The solvent was removed under vacuum, and the residue was purified by flash chromatography on a silica gel column using a 10-50% ethyl acetate-hexane solvent system to yield N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine (12.
9 g, 62.
5 mmol, 75% yield).
Step 2: Reduction of N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine to Methyl 3-[[(2-methoxy-2-oxoethyl)amino]sulfonyl]-2-thiophenecarboxylate
To a solution of N-Methyl-N-[[(2-methoxy-2-oxoethyl)sulfonyl]amino]-L-alanine (12.
9 g, 62.
5 mmol) in toluene (100 mL), a solution of potassium permanganate (1.
26 g, 5.
63 mmol) in water (20 mL) was added, and the reaction was stirred for 2 hours.
The reaction was then quenched with sodium carbonate solution, and the organic layer was separated and dried over anhydrous sodium sulfate.
The solvent was removed under vacuum, and the residue was purified by flash chromatography on a silica gel column using a 20-80% ethyl ac
