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Chemical Structure| 51219-55-7 Chemical Structure| 51219-55-7
Chemical Structure| 51219-55-7

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3-(((Benzyloxy)carbonyl)amino)-3-methylbutanoic acid

CAS No.: 51219-55-7

4.5 *For research use only!

Cat. No.: A327747 Purity: 95%

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Product Details of [ 51219-55-7 ]

CAS No. :51219-55-7
Formula : C13H17NO4
M.W : 251.28
MDL No. :MFCD18206364

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Application In Synthesis [ 51219-55-7 ]

* 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 [ 51219-55-7 ]

[ 51219-55-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 625-05-8 ]
  • [ 501-53-1 ]
  • [ 51219-55-7 ]
YieldReaction ConditionsOperation in experiment
46% Step A: Synthesis of 3-benzyloxycarbonylamino-3-methyl-butyric acid. 3-Amino-3-methylbutyric acid (2.40 g, 20.49 mmol) was dissolved in NaOH (2 M aq, 35 mL), the resulting mixture cooled to 0° C., and benzyl chloroformate (5.77 mL, 40.97 mmol) added. The reaction mixture was stirred vigorously at 0° C. for 1 h and at RT for 3 h. Et2O (50 mL) was then added, and the layers separated. The organic layer was discarded. The aqueous layer was acidified to pH 2, brine added, and the resulting mixture extracted with EtOAc. The combined organic extracts were dried over anhydrous Na2SO4, filtered and evaporated under reduced pressure to give 3-benzyloxycarbonylamino-3-methyl-butyric acid (2.33 g, 46percent yield) without further purification.
  • 3
  • [ 13139-17-8 ]
  • [ 625-05-8 ]
  • [ 51219-55-7 ]
YieldReaction ConditionsOperation in experiment
65.7% With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20℃; for 17.5h; N-(Benzyloxycarbonyloxy)succinimide (24.4 g, 1 equiv, 98 mmol) was added to a solution of <strong>[625-05-8]3-amino-3-methylbutanoic acid</strong> (16.0 g, 97.2 mmol) in methanol and water (200 mL: 100 mL) followed by the addition of THF (100 mL) to give a clear solution. <n="86"/>The solution was cooled in an ice bath for 15 min and a solution of 5 N sodium hydroxide (39 mL, 2 equiv) was added over 15 min. The solution was stirred at 0 0C for an additional hour and stirred at RT for 17 h. The organic solvent was removed and the aqueous was extracted with ethyl acetate (2x 200 mL). The aqueous layer was acidified with 6 N HCl (50 mL) and extracted with ethyl acetate (4x 200 mL). The organic layer was dried over anh. MgSO4, filtered, and concentrated to an orange yellow oil (16.2 g, 65.7percent). This oil was used without further purification. LRMS (ESI -ve) for Ci3H17NO4 (251.1); found: 250.
 

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