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182009-04-7

PeMetrexed EP IMpurity E synthesis

1synthesis methods
PeMetrexed EP IMpurity E

182009-04-7
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N-[4-[2-(2-AMino-4,5,6,7-tetrahydro-4,6-dioxo-1H-pyrrolo[2,3-d]pyriMidin-5-yl)ethyl]benzoyl]-L-glutaMic Acid

193281-00-4
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Yield:193281-00-4 89%

Reaction Conditions:

with Cumene hydroperoxide;C39H38AuN6(1+)*Cl(1-) in water;1,2-dichloro-ethane at 50; for 3.5 h;Reagent/catalyst;Solvent;Temperature;

Steps:

1-4

Put 5mmol pemetrexed,0.4mmol catalyst 2, 6mmolCumene hydroperoxide, 15mL dichloroethane and 1.1mL water were added to the reaction flask, stirred evenly and then heated to 50°C, and stirred at this temperature for about 3.5h. The end of the reaction was detected by TLC, and the heating was stopped. The reaction system was cooled to room temperature, filtered, and the organic layer was separated and extracted with 15 mL of dichloroethane three times. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting oily substance was subjected to column chromatography (acetic acid Ethyl: methanol = 5:1) to obtain the compound of formula (I) N-[4-[2-(2-amino-4,6-dioxo-4,5,6,7-tetrahydro-3H -Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]glutamic acid is an off-white solid with a yield of 89%. The structure of the target product was confirmed by MS and 1H NMR, and the high-pressure liquid phase detection showed that the purity was greater than 98%

References:

CN111592547,2020,A Location in patent:Paragraph 0021-0032

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