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Chemical Structure| 227805-38-1 Chemical Structure| 227805-38-1

Structure of 227805-38-1

Chemical Structure| 227805-38-1

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Product Details of [ 227805-38-1 ]

CAS No. :227805-38-1
Formula : C14H25NOSi
M.W : 251.44
SMILES Code : C[Si](OCCNC1=CC=CC=C1)(C(C)(C)C)C

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Application In Synthesis of [ 227805-38-1 ]

* 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 [ 227805-38-1 ]

[ 227805-38-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 22744-12-3 ]
  • [ 227805-38-1 ]
  • [ 1429653-12-2 ]
YieldReaction ConditionsOperation in experiment
90% With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;Inert atmosphere; EDC (114.5mg, 0.597 mmol) was added to a solution containing N- (2- ( ( ert-butyldimethylsilyl) oxy) ethyl) aniline 3 (100 mg, 0.398 mmol) and 2- (4- (methoxycarbonyl) phenyl) acetic acid, 8, (116 mg, 0.597 mmol) in CH2C12 (3 mL) . The reaction mixture was stirred overnight at room temperature in argon atmosphere. After completion of reaction the reaction mixture was diluted with mixed solvent (CHC13 : i-PrOH = 4:1, 10 mL) and washed with sat. NH4C1. The organic layer was dried (anhydrous sodium sulfate) and concentrated in vacuo. The crude product was chromatographed on silica gel (Hexanes/EtOAc, 7:1) to yield target compound 4. Yield 306 mg, 90%. Rf = 0.36, XH NMR (CHC13, 400 MHz): delta 7.91 (d, J= 8.2, Hz, 2H) , 7.38 (m, 3H) , 7.15 (m, 4H) , 3.91 (s, 3H) , 3.80 (m, 4H) , 3.50 (s, 2H) , 0.85 (s, 9H) , 0.02 (s, 6H) ; 13C NMR (CHC13, 100 MHz): delta 170.2, 167.0, 142.9, 140.8, 129.6, 129.5, 129.1, 128.6, 128.5, 128.0, 60.1, 52.1, 52.0, 41.4, 25.8, 18.2, -5.4; [M+H]+ = 427.84 (APCI+) . 4- (2- ( (2- { ( tert-butyIdimethyl ai1yl) oxy) ethyl) (phenyl) amino) -2- oxoethyl) -N-hydroxybenzamide (5): Hydroxylamine (0.5 mL, 50% water solution) was added to a solution containing methyl 4- (2- ( (2- ( (tert- butyldimethylsilyl) oxy) ethyl) (phenyl) amino) -2-oxoethyl) benzoate 4 (60 mg, 0.140 mmol) in THF/MeOH (1:1, 1 mL) . Reaction mixture was treated with cat. amount of KCN (-0.5 mg) and stirred at room temperature in argon atmosphere for 16 h. Then solution was acidified by NH4C1/HC1 solution to pH 4. The mixture was diluted with mixed solvent (CHC13 : i-PrOH = 4:1, 10 mL) and washed with sat. NH4C1. The organic layer was dried (anhydrous sodium sulfate) and concentrated in vacuo. The crude product was purified by preparative chromatography on silica gel (CH2Cl2/ eOH, 10:1) to yield target compound 5. Yield 40 mg, 66%. Rf = 0.36, H NMR (CD3OD, 400 MHz): delta 7.64 (d, J = 8.4 Hz, 2H) , 7.45 (m, 3H) , 7.28 (d, J = 8.0 Hz, 2H) , 7.13 (d, J = 8.0 Hz, 2H) , 3.80 (m, 4H) , 3.54 (s, 2H) , 0.88 (s, 9H) , 0.05 (s, 6H) ; .13C NMR (CD3OD, 100 MHz): delta 172.0, 167.0, 142.6, 139.7, 130.8, 129.7, 128.8, 128.4, 127.6; 126.2, 60.7, 52.0, 41.0, 26.2, 18.0, -5.4; [M+H]+ = 428.85 (APCI+) .
 

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