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Chemical Structure| 154462-98-3 Chemical Structure| 154462-98-3

Structure of 154462-98-3

Chemical Structure| 154462-98-3

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Product Details of [ 154462-98-3 ]

CAS No. :154462-98-3
Formula : C7H16N2O
M.W : 144.21
SMILES Code : CC(C)[C@H](N)C(N(C)C)=O

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Application In Synthesis of [ 154462-98-3 ]

* 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 [ 154462-98-3 ]

[ 154462-98-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 23361-28-6 ]
  • [ 154462-98-3 ]
  • tert-butyl N-[(2S)-1-[(2S)-2-[(1S)-1-(dimethylcarbamoyl)-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
99% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 25℃; for 20h;Inert atmosphere; General procedure: Compound 7a (1 equiv.) was dissolved in 7 mL DMF. To this was added HBTU (1.2 equiv.) and DIEA (2.5 equiv.) to generate the activated ester. After 10 min, 23a-d (1.5 equiv.) was added and the reaction mixture was stirred under nitrogen overnight. The reaction was diluted with EtOAc (50 mL) and an equal amount of NaHCO3, washed with brine (6×50 mL), dried (MgSO4) and concentrated under vacuum.The crude product was subjected to column chromatography(100% EtOAc) which yielded 24a-d. Tert-butyl-N-[(2S)-1-[(2S)-2-[(1S)-1-(dimethylcarbamoyl)-2-methylpropyl]carbamoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]carbamate (24a). Using the procedure described for the synthesis of Peptidyl N-methylamides,0.25 g (0.81 mmol) of 7a was coupled to 0.17 g(1.18 mmol) of 23a to yield a colourless oil which formed a white solidfoam under reduced pressure (0.35 g, 99%). HPLC tr=12.232 min. 1HNMR (400 MHz, CDCl3) δ 7.04 (d, J=8.8 Hz, 1H), 5.35 (d, J=9.3 Hz,1H), 4.73 (dd, J=8.8, 6.3 Hz, 1H), 4.51 (dd, J=8.0, 3.4 Hz, 1H), 4.27(dd, J=9.4, 5.9 Hz, 1H), 3.74-3.57 (m, 2H), 3.06 (s, 3H), 2.93 (s, 3H),2.15-2.06 (m, 2H), 2.02-1.89 (m, 4H), 1.39 (s, 9H), 0.97 (d,J=6.8 Hz, 3H), 0.93-0.81 (m, 9H). 13C NMR (101 MHz, CDCl3) δ171.8, 171.5, 171.1, 155.9, 79.3, 60.1, 56.7, 53.6, 47.5, 37.3, 35.6,31.7, 31.4, 28.3, 28.26, 25.1, 19.5, 19.5, 17.6, 17.2. ESI-MS (m/z):calcd for C22H40N4NaO5 (M+Na) m/z 463.2896 found 463.2903.
 

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