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Chemical Structure| 126937-42-6 Chemical Structure| 126937-42-6

Structure of 126937-42-6

Chemical Structure| 126937-42-6

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Product Details of [ 126937-42-6 ]

CAS No. :126937-42-6
Formula : C19H26N2O6
M.W : 378.42
SMILES Code : O=C(N1C(C(OC)=O)CN(C(OC(C)(C)C)=O)CC1)OCC2=CC=CC=C2
MDL No. :MFCD03426296
InChI Key :FUMOVDZJNXKHJM-UHFFFAOYSA-N
Pubchem ID :4451965

Safety of [ 126937-42-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 126937-42-6 ]

* 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 [ 126937-42-6 ]

[ 126937-42-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 126937-42-6 ]
  • [ 129799-08-2 ]
YieldReaction ConditionsOperation in experiment
95% With hydrogen;palladium 10% on activated carbon; In methanol; at 20℃; for 3h; Step 3: 1-ferf-butyl 3-methyl piperazine-l,3-dicarboxylate (A3); 10% Pd-C (0.2 eq) was added to a stirred RT 0.1 M solution of A2 in MeOH and the mixture was stirred under an H2 atmosphere at RT for 3 h. The mixture was filtered, washing with MeOH, and the filtrate was evaporated under reduced pressure to give the title compound in 95 % yield. 1H NMR (400 MHz, CDCl3, 300K) delta 4.02 (IH, m), 3.74 (3H, s), 3.70 (IH, m), 3.43 (IH, m), 3.20 (IH, m), 3.04 (2H, m), 2.75 (IH, m), 2.14 (IH, m), 1.47 (9H, s). MS (ES+) CnH20N2O4 requires 244, found: 267 (M+Na)+.
With hydrogen;palladium 10% on activated carbon; In ethanol; for 18h; A solution of Intermediate 1 (1.0 g, 2.64 mmol) in ethanol (15 mL) was added under a nitrogen atmosphere to wetted palladium, 10 wt. % on activated carbon (0.2 g). The reaction mixture was placed under an atmosphere of hydrogen and stirred vigorously for 18 hours. The mixture was filtered through Celite under a nitrogen atmosphere and the filtrate was evaporated to give the title compound as an oil. MS calcd for (CllH2oN204 + H) + : 245. Found: (M+H) + = 245.
In methanol; palladium-carbon; Step B Methyl 4-tert-butoxycarbonylpiperazine-2-carboxylate A solution of the product from step A in methanol was hydrogenated at 60 psi in the presence of 10% Pd/C (0.250 g) for 24h. The catalyst was filtered and the methanol evaporated to yield the title compound as an oil (0.91 g).
A. Piperazine-1.3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester According to General Procedure F, piperazine-1,2,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester 2-methyl ester (3.0 g, 7.0 mmol) was deprotected to give the title compound of part 5-A (1.8 g, 94%: +APcl MS (M+H)+ 245; 1H NMR=400 MHz (CDCl3) iota: (Me, s, 3H), 3.43 (dd, 1H), 2.73 (t, 1H), 1.45 (BOC, s, 9H).
With palladium 10% on activated carbon; hydrogen; In methanol; under 15001.5 Torr; 1-benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (10.0 g, 73.0 mmol) was dissolved in 150 ml of methanol and eluted over a cartridge of 10% PdJC charged with H2 at a pressure of 20 bar. The eluent was then concentrated in vacuo to afford the crude desired product.
6.0 g (99%) palladium-carbon; In methanol; Step 4: The preparation of piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester: Piperazine-1,2,4-tricarboxylic acid, 4-(1,1-dimethylethyl) 2-methyl 1-(phenylmethyl) ester (9.0 g, 23.8 mmol) was treated with MeOH (100 mL) and 20% Pd/C (1.0 g) and shaken under an atmosphere of H2. The reaction was filtered and concentrated to give 6.0 g (99%) of the desired product. MS: 245 (M+1 for C11H20N2O4).

  • 2
  • [ 126937-42-6 ]
  • [ 126937-43-7 ]
YieldReaction ConditionsOperation in experiment
Intermediate 21 : 2-Methyl-1-(phenylmethyl) 1,2-piperazinedicarboxylate. 2-Methyl 1-(phenylmethyl) 1 ,2-piperazinedicarboxylate was prepared from the corresponding TFA salt (whose preparation is already known in literature eg. in Journal of Medicinal Chemistry (1990), 33(10), 2916-24 or Tetrahedron Letters (1989), 30(39), 5193-6.) To a DCM solution (5ml) of (4-(1,1 -dimethylethyl) 2-methyl 1-(phenylmethyl) 1 ,2,4-piperazinetricarboxylate (500mg) was added, at 00C, TFA (3ml) and the reaction temperature allowed to slowly reach 200C. After complete conversion of the starting material DCM was evaporated, the crude was dissolved in water and extracted with Et2O; then the water phase was basified (pH>9) with solid NaOH and extracted with DCM, the organic layer dried over Na2SO4 and the solvent evaporated to give a colourless oil (92 mg);UPLC RT=0.47; m/z (ES): 279.1 [M+H]+; H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.29 - 7.45 (m, 5 H) 5.09 - 5.25 (m, 2 H) 4.60 - 4.83 (m, 2 H) 3.85 - 4.05 (m, 1 H) 3.69 - 3.84 (m, 3 H) 3.44 - 3.63 (m, 1 H) 2.87 - 3.33 (m, 3 H) 2.65 - 2.84 (m, 1 H).
  • 3
  • [ 501-53-1 ]
  • [ 129799-08-2 ]
  • [ 126937-42-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 1h; Step 1 Piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (244 mg, 1.0 mmol) was dissolved in 5 mL of dichloromethane followed by sequential addition of TEA (202 mg, 2.0 mmol) and benzyl chloroformate (170 mg, 1.0 mmol) at room temperature. After the reaction was stirred for 1 hour, it was diluted with dichloromethane, and then washed with water and brine. The solvent was concentrated to give crude Compound Y, which was used directly without further purification.
With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 5 - 35℃; for 14h; Benzyl carbonochloridate (6.43 mL, 45.03 mmol) was added to a solution of <strong>[129799-08-2]1-tert-butyl 3-methyl piperazine-1,3-dicarboxylate</strong> (10 g, 40.94 mmol) and DIEA (14.30 mL, 81.87 mmol) in THF (100 mL) at 5C, and the mixture was stirred at room temperature for 14 hr. The reaction mixture was added to water and ethyl acetate. The organic layer was washed with aqueous ammonium chloride solution, dried over magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 5?20% ethyl acetate/hexane) to give 1-benzyl 4-tert-butyl 2-methyl piperazine-1,2,4-tricarboxylate (16.2 g, 42.8 mmol, 105%) as white crystals. 1H NMR (300 MHz, CDCl3):delta 1.44(9H,s), 2.63-3.48(3H,m), 3.74(3H,s), 4.11(2H,s), 4.44-4.86(2H,m), 5.08-5.26(2H,m), 7.22-7.42(5H,m).
 

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