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Chemical Structure| 45022-27-3 Chemical Structure| 45022-27-3

Structure of 45022-27-3

Chemical Structure| 45022-27-3

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Product Details of [ 45022-27-3 ]

CAS No. :45022-27-3
Formula : C8H12O4
M.W : 172.18
SMILES Code : O=C(O)/C=C\C(OC(C)(C)C)=O
MDL No. :N/A

Safety of [ 45022-27-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501

Application In Synthesis of [ 45022-27-3 ]

* 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 [ 45022-27-3 ]

[ 45022-27-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5835-79-0 ]
  • [ 45022-27-3 ]
  • [ 1448896-84-1 ]
YieldReaction ConditionsOperation in experiment
General procedure: General Procedure C Preparation of Mono-Esters of Fumaric Acid Coupling Reaction of Morpholin-4-ylalkyl-1-ol with Fumaric Acid [0429] [0430] Fumaric acid (1.0 eq.) is dissolved in an inert solvent such as dichloromethane (DCM), N,N-dimethylformamide (DMF), N-methylpyrrolidone (NMP), or N,N-dimethylacetamide (DMA, DMAc) (ca. 3 mL/mmol) and the solution is treated with 1.0-1.5 eq. of a carbodiimide dehydration agent such as 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDAC, EDC), N,N-diisopropylcarbodiimide (DIC), N,N-dicyclohexyl-carbodiimide (DCC) at a temperature from ca. 0 C. (ice bath) to room temperature. The mixture is then reacted with a solution of an appropriately functionalized of morpholin-4-ylalkyl-1-ol (1.0-1.5 eq.) in the same solvent. Optionally, a catalytic or stoichiometric amount of 4-(N,N-dimethylaminopyridine (DMAP) is added to the mixture at a temperature from ca. 0° C. to room temperature. When the amine is in a salt form, an equimolar amount of an organic tertiary base, such as triethylamine (TEA), or diisopropylethylamine (DIEA) may be added to free the amine base prior to the coupling step. The reaction mixture is stirred for 4 to 12 hours at room temperature. Optionally the organic solvents are removed under reduced pressure using a rotary evaporator and the residue diluted with an appropriate extraction solvent such as diethyl ether (Et2O), methyl tert-butyl ether (MTBE), ethyl acetate (EtOAc), or others. Water is added to the reaction mixture, the aqueous phase was acidified using 1N hydrochloric acid until aqueous pH reaches to pH 2. After phase separation, the aqueous phase is extracted several times with the same solvent. The combined organic extracts are washed with water, brine, and dried over anhydrous magnesium sulfate (MgSO4). After filtration, the organic solvents are removed under reduced pressure using a rotary evaporator. If required, the crude reaction products are further purified by well-known purification techniques such as silica gel flash column chromatography (i.e., Biotage), mass-guided reversed-phase preparative HPLC/lyophilization, precipitation, or crystallization to yield the pure desired product. Example 15 (4-Morpholinobutyl)fumarate (39) [0471] t-butyl hydrogen fumarate (MHF) (0.2 mol) is activated with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDAC) (47.75 g, 0.25 mol) in 200 mL of dichloromethane (DCM) at ca. 0 C. 4-Morpholin-4ylbutyl-1-ol (31.8 g, 0.2 mol) and 4-N,N-dimethylaminopyridine (DMAP) (1 g, 0.008 mol) were added to the activated carboxylic acid. After work-up and isolation, the crude material is reacted with 50% vol-% trifluoroacetic acid in DCM. The free acid is purified by mass-guided preparative HPLC to afford the title compound (40).
 

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