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Chemical Structure| 13602-96-5 Chemical Structure| 13602-96-5

Structure of 13602-96-5

Chemical Structure| 13602-96-5

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Product Details of [ 13602-96-5 ]

CAS No. :13602-96-5
Formula : C12H15NO4
M.W : 237.25
SMILES Code : O=C(OCC)C1=CC(C(OCC)=O)=C(C)N=C1
MDL No. :MFCD13189606

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Application In Synthesis of [ 13602-96-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 13602-96-5 ]

[ 13602-96-5 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 80370-42-9 ]
  • [ 13602-96-5 ]
  • 2
  • [ 80370-42-9 ]
  • [ 626-34-6 ]
  • [ 13602-96-5 ]
YieldReaction ConditionsOperation in experiment
32 g To a mixture of <strong>[80370-42-9]ethyl 2-formyl-3-oxopropanoate</strong> (50.0 g) and diethyl ether (350 mL) was added dropwise TEA (38.5 g) at - 10°C. The reaction mixture was stirred at 25°C for 2 hr. The solvent was evaporated under reduced pressure, and a solution of 4-methylbenzenesulfonyl chloride (72.9 g) in DMF (200 mL) was added thereto with stirring at -20°C. The reaction mixture was warmed to 25°C, and stirred for 4 hr. To the mixture was added a solution of ethyl (2Z) -3-aminobuta-2-enoate (47.1 g) and pyridine (109 g) in DMF (150 mL) at 25°C. The reaction mixture was stirred at 80°C for 10 hr. The reaction mixture was concentrated under reduced pressure, the residue was diluted with saturated aqueous sodium hydrogencarbonate solution (500 mL), and the mixture was extracted with ethyl acetate (600 mL x 2). The combined organic layer was washed with saturated brine (1000 mL x 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (32.0 g). MS: [M+H]+237.9.
  • 3
  • [ 80370-42-9 ]
  • [ 626-34-6 ]
  • [ 13602-96-5 ]
YieldReaction ConditionsOperation in experiment
Ethyl 2-formyl-3-oxopropanoate (500.0 g) was dissolved in DMF (1.50 L) , and the solution was cooled to 0°C. To the solution were added TEA (702.0 g) and 4-methylbenzenesulfonyl chloride (728.0 g) at 0°C, and the mixture was stirred under nitrogen atmosphere at 15°C for 1 hr. To the mixture were added molecular sieve 4A (500.0 g) , pyridine (1.10 kg) and a solution of ethyl 3-aminobuta-2-enoate (448 g) in DMF (1 L) at 15°C, and the mixture was stirred at 80°C under nitrogen atmosphere for 12 hr. The same procedure was carried out a total of ten times in parallel, all the mixtures were cooled to 15°C, the mixtures were combined, and the solid was removed by filtration. The filtrate was poured into saturated aqueous sodium hydrogencarbonate solution (50 L) , and the mixture was extracted with tert-butyl methyl ether (20 L and 10 L) . The combined organic layers were washed with saturated brine (10 L) , dried over anhydrous sodium sulfate, and concentrated under reduced pressure. To the residue was added petroleum ether (5 L) , the mixture was stirred, and the precipitated solid was collected by filtration. The obtained solid was purified by silica gel column chromatography (petroleum ether/ethyl acetate) to give the title compound (2.50 kg). XH NMR (400 MHz, DMSO-d6) delta 1.32-1.36 (6H, m) , 2.79 (3H, s) , 4.33-4.39 (4H, m) , 8.55 (1H, d, J = 1.6 Hz), 9.08 (1H, d, J = 2.0 Hz) .
 

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