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Chemical Structure| 134307-72-5 Chemical Structure| 134307-72-5

Structure of 134307-72-5

Chemical Structure| 134307-72-5

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Product Details of [ 134307-72-5 ]

CAS No. :134307-72-5
Formula : C11H15NO5S
M.W : 273.31
SMILES Code : O=C(OCC1=CC=CC=C1)NCCOS(=O)(C)=O

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Application In Synthesis of [ 134307-72-5 ]

* 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 [ 134307-72-5 ]

[ 134307-72-5 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 14381-51-2 ]
  • [ 134307-72-5 ]
  • [ 1095422-53-9 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 4h; The l-bromo-2,3-dimethoxybenzene (2.17 g, 10 mmol) was dissolved in DCM (60 ml) and treated with 1.0 M DCM solution OfBBr3 (15 mL, 15 mmol) at 0 °C and then allowed to warm to room temperature. After stirring overnight, the reaction mixture was cooled to 0 0C, 2 mL of MeOH was added, and the solvent was removed under vacuum. The residue was dissolved in 20 mL of EtOAc and washed with IN HCl (2 x 50 mL), water, brine and dried over Na2SO4. The solvent was removed under vacuum. The crude residue was then dissolved in DMF (40 mL) and Cs2CO3 (9.75 g, 30 mmol) and 2- (benzyloxycarbonylamino)ethyl methanesulfonate (6.8 g, 25 mmol) were added. After stirring at 100 0C under nitrogen for 2 h, a further amount OfCs2CO3 (9.75 g, 30 mmol) and 2-(benzyloxycarbonylamino)ethyl methanesulfonate (6.8 g, 25 mmol) were added. After stirring at 100 0C for 2 h, the reaction mixture was poured onto water (900 mL) and extracted with EtOAc (3 x 100 mL). The organic layers were combined, washed with water (50 mL) and dried over Na2SO4. The solvent was removed under vacuum and purified by flash chromatography using cyclohexane/EtOAc (8/2) as eluent to afford the title compound (2.45 g, 45percent yield) as a white solid. <n="54"/>ESMS; m/z 543, 545 (M+l), 560, 562 (M+18)1H-NMR (CDCl3): 63.54 (m, 4H), 4.06 (m, 4H), 5.09 (s, 4H), 5.62(bs, IH), 5.75(bs, IH), 6.82 (d, J= 8 Hz, IH), 6.91 (t, J= 8 Hz, IH), 7.13 (dd, J= 8 Hz, J= 1.3 Hz, IH), 7.32 (m, 10H). 13C-NMR (CDCl3): 540.5, 41.3, 66.8, 68.2, 71.8, 112.9, 118.0, 125.4, 128.1, 128.2, 128.5, 136.4, 152.6, 156.5.Theoretical Mass: (M + Na) 565.09501. Measured Mass: (M + Na) 565.09508 Microanalysis: percentC 57.58 (57.47), percentH 5.10 (5.01), percentN 5.16 (5.04) M.p. 54°C
  • 2
  • [ 134307-72-5 ]
  • [ 67104-97-6 ]
  • [ 1261242-16-3 ]
YieldReaction ConditionsOperation in experiment
42.9% Under nitrogen atmosphere, the compound 6a (0.856 g, 6.26 mmol) was dissolved in 5 mL of anhydrous DMSO,and 60% NaH (0.282 g, 11.8 mmol) was slowly added dropwise at 0C. The temperature was raised to room temperature,and then the solution was stirred for 1 hour. 2-(((benzyloxy)carbonyl)amino)ethyl methane sulfonate (1.5 g, 5.83 mmol)was slowly added dropwise at 0 C, and then stirred at room temperature for 5 hours. After the reaction was completed,extraction was performed with ethyl acetate, and an organic solvent layer was dried over MgSO4. Filtration was performedto remove the solvent, and a residue was purified by column chromatography (EtOAc) to obtain a compound 7a (0.82 g). Sticky oil (42.9%). 1H-NMR (CDCl3, 300MHz) delta7.36-7.30 (m, 5H), 5.19 (bs, 1H), 5.10 (s, 2H), 3.46 (q, 2H, J = 5.9 Hz), 3.36-3.26 (m, 4H), 3.20 (t, 2H, J = 6.0 Hz). LC-MS: Predicted value calculated with respect to C13H19N3O4S m/z: 313. Measured value: 314(M+1)+.
 

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