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Chemical Structure| 156892-82-9 Chemical Structure| 156892-82-9

Structure of 156892-82-9

Chemical Structure| 156892-82-9

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Product Details of [ 156892-82-9 ]

CAS No. :156892-82-9
Formula : C12H18N2O2
M.W : 222.28
SMILES Code : O=C(OCC1=CC=CC=C1)NCC(C)(N)C
MDL No. :MFCD11041339

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* 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 [ 156892-82-9 ]

[ 156892-82-9 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 28170-07-2 ]
  • [ 811-93-8 ]
  • [ 156892-82-9 ]
YieldReaction ConditionsOperation in experiment
87% Example 2: Synthesis of compound 22.28 g (10 mmol) benzyl phenylcarbonate was dissolved in 20 ml ethanol and 1.03 ml (10 mmol) 1,2-diamino-l-methylpropane was added dropwise and stirred at RT overnight. The mixture was diluted with 25 ml water and acidified with 1M HC1 until pH < 3 and extracted with DCM. The aqueous phase was basified with 4M NaOH and extracted with DCM. The extract was dried with MgS04 and concentrated in vacuo. This gave 1.93 g (87%) monoprotected diamine. This material was dissolved in 25 ml dioxane, 2.028 g (10.5 mmol) Boc20 and 0.12 g (1 mmol) DMAP were added and the reaction was stirred at RT overnight. The mixture was concentrated in vacuo and purified by column chromatography (Si02, ether/heptane, 1 :0 to 7:3) to give 1.13 g (40%) of diprotected diamine. The diprotected diamine was dissolved in 10 ml dry DMF, 1.1 ml (17.5 mmol) iodomethane was added and the reaction mixture cooled in ice. 0.50 g (10.5 mmol) sodium hydride (60% in oil) was added in portions and stirred in ice for 2 hrs. The mixture was warmed to RT, quenched with 10 ml saturated NH4C1 and 50 ml water, extracted with ethyl acetate, dried with MgS04 and concentrated in vacuo. The product was purified by column chromatography (Si02, DCM/ethyl acetate, 1 :0 to 50:1) to give 0.358 g (29%) of Cbz-protected compound 2. 1H-NMR (300 MHz, CDC13): delta = 1.29 (s, 3H, Me), 1.35 (s, 3H, Me), 1.46 (s, 9H, Boc), 2.82/2.86 (s, 3H, Me, Z/E), 2.93 (s, 3H, Me), 3.72 (s, 2H, CH2N), 5.12 (s, 2H, benzyl), 7.35 (m, 5H, Phe). This material was dissolved in 20 ml methanol, 0.04 g Pd/C was added, the mixture was stirred under hydrogen for 3 hrs, filtered, and the filtrate concentrated. This gave 0.21 g (100%) of compound 2. MS (ESI): m/z = 217.2 (M+H+).
 

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