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Chemical Structure| 192212-24-1 Chemical Structure| 192212-24-1

Structure of 192212-24-1

Chemical Structure| 192212-24-1

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Product Details of [ 192212-24-1 ]

CAS No. :192212-24-1
Formula : C14H22N2O4
M.W : 282.34
SMILES Code : O=C(NCCCCCN1C(C=CC1=O)=O)OC(C)(C)C
MDL No. :MFCD22682785

Safety of [ 192212-24-1 ]

Application In Synthesis of [ 192212-24-1 ]

* 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 [ 192212-24-1 ]

[ 192212-24-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 55750-49-7 ]
  • [ 192212-24-1 ]
YieldReaction ConditionsOperation in experiment
68% In tetrahydrofuran; sodium carbonate; b) N-(tert.butyloxycarbonyl)-5-(N-maleinimido)pentylamine 13.1 g (50 mmol) of the compound prepared according to Example 1b is dissolved in 250 ml saturated sodium carbonate solution. The solution is filtered over a folded filter and cooled to 0 C. 8.4 g (50 mmol) N-(ethoxycarbonyl)-maleinimide is added while stirring and is left to stir for a further 15 min at room temperature, during which the N-(ethoxycarbonyl)-maleinimide dissolves completely after a short time. Subsequently 400 ml tetrahydrofuran is added together with 250 ml saturated sodium carbonate solution and it is allowed to react for a further 1 h. The solution is then extracted with 2*500 ml acetic ester, the extract is washed with 500 ml water and dried with 50 g Na2 SO4. After evaporation in a rotary evaporator the product is obtained as a viscous oil which is dried in a high vacuum. Yield: 9.6 g (corresponds to 68% of the theoretical yield). TLC: silica gel, n-butanol/glacial acetic acid/water 40/10/50 (v/v/v), spray with 0.1% KMnO4 solution; Rf =0.85.
  • 2
  • [ 55750-49-7 ]
  • [ 462-94-2 ]
  • [ 24424-99-5 ]
  • [ 192212-24-1 ]
YieldReaction ConditionsOperation in experiment
94 mg To a solution of 1,5-diaminopentane (0.86 g, 8.5 minol) in water (100 mL) at 0 C was added dropwise a solution of di-tert-butyl dicarbonate (0.46 g, 2.1 minol) in 1,4-dioxane (150 mL), and the mixture stirred at room temperature for 16 h. The mixture was then concentrated by half in vacuo, filtered, and the filtrate extracted with ethyl acetate (3 x). The combined organic layers were then dried over anhydrous magnesium sulfate, filteredand the solution concentrated in vacuo to afford a yellow oil, which was used without further purification. To a solution of the crude oil in saturated aqueous sodium bicarbonate (8 mL) at 0 C was added 45 (248 mg, 1.0 minol), and the mixture stirred at 0 C for 30 minutes. A solution of acetonitrile/water (16 mL, 1:1 v/v) was then added and the mixture stirred at room temperature for 4 h. The mixture was then extracted with dichloromethane (3 x), thecombined organic layers dried over anhydrous magnesium sulfate, filtered and the solutionconcentrated in vacuo. Purification by column chromatography (EtOAc/hexanes, 1:2)afforded the title compound 57 (94 mg, 40%) as a colourless oil. 1H NMR (400 MHz, CDCI3)oe 1.26-1.31 (2H, m, H-3?), 1.42 (9H, s, Boc), 1.45-1.52 (2H, m, H-2?), 1.55-1.63 (2H, m,H-4?), 3.06-3.09 (2H, m, H-i?), 3.50 (2H, t, J = 7.2 Hz, H-5?), 4.50-4.55 (1H, m, NH), 6.67(2H, s, H-3, H-4); 13C NMR (100 MHz, CDCI3) oe 23.9 (CH2, C-3?), 28.2 (CH2, C-4?), 28.4 (3x CH3, Boc), 29.5 (CH2, C-2?), 37.6 (CH2, C-5?), 40.3 (CH2, C-i?), 79.0 (C, Boc), 134.1 (2 xCH, C-3, C-4), 156.0 (C, Boc), 170.8 (2 x C, C-2, C-5); vmax (cm1) 3365, 2939, 1698,1675, 1529, 1412, 1272, 1165, 1117, 832, 695; HRMS-ESI [M+Na] Calcd. forC14H22N2O4Na 304.1472, found 305.1467.
 

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