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Chemical Structure| 109180-95-2 Chemical Structure| 109180-95-2

Structure of 109180-95-2

Chemical Structure| 109180-95-2

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Product Details of [ 109180-95-2 ]

CAS No. :109180-95-2
Formula : C14H23NO5
M.W : 285.34
SMILES Code : O=C([C@H]1N(C(OC(C)(C)C)=O)CCC1)CC(OCC)=O
MDL No. :MFCD11975759

Safety of [ 109180-95-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Application In Synthesis of [ 109180-95-2 ]

* 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 [ 109180-95-2 ]

[ 109180-95-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 4565-31-5 ]
  • [ 109180-95-2 ]
  • [ 603999-21-9 ]
YieldReaction ConditionsOperation in experiment
With piperidine; In DMF (N,N-dimethyl-formamide); at 80℃; for 0.75h; A DMF (10 mL) solution of tert-Butyl (2S)-2-(3-ethoxy-3-oxopropanoyl)-1- pyrrolidinecarboxylate (2.85 g, 9.99 mmol), 2-formyl-5-thiophene carboxylic acid (1.56 g, 9.99 mmol) and piperidine (0.494 mL, 5.00 mmol) was heated to 80°C for 45 min and then cooled to ambient temperature. The reaction mixture was diluted with Et20 and washed 1 N HCl, 2 x H20, 1 x brine and the organics dried (Na2S04), filtered and concentrated to a brown residue. The Knoevenagel product (4.23 g, 9.99 mmol) and ethyl (2Z)-3-amino-5- (4-fluorophenyl)-2-pentenoate (2.37 g, 9.99 mmol) were heated to 110°C for 1. 5h and then cooled to ambient temperature. The glassy solid was redissolved in CH3CN (20 mL) and H20 (20 mL) followed by addition of ceric ammonium nitrate (10.95 g, 19.98 mmol). The reaction mixture stirred for 45 min at ambient temperature and then Et20 was added and the organics extracted and washed 1 x H20, 1 x brine, and then dried (Na2SO4), filtered and concentrated to a dark tan solid. The solid from the previous reaction was subjected to TFA (15 mL in 4 mL CH2CI2) for 1 h and then concentrated. The residue was redissolved in CH2C12 (20 mL) and treated with Et3N (12 mL). After 16 h the reaction mixture was concentrated to a brown foam. The residue was redissolved in CHC13 and washed 1 x pH 4.5 buffer, 1 x brine and the organics dried (Na2SO4), filtered and concentrated. Chromatography on silica gel using 9: 1 EtOAc: MeOH eluted the desired compound as a yellow solid (2.16 g, 4. 37 mmol) 44percent yield :'H NMR (CDCl3, 400 MHz) 8 7.70 (d, J=3. 7Hz, lH), 7.19-7. 14 (m, 3H), 6.96 (t J = 8.7 Hz, 2H), 4.70 (dd, J= 10.2, 6.2 Hz, 1H), 4. 15 (dd, J= 14.2, 7.1 Hz, 2H), 3.81-3. 71 (m, 1H), 3.43-3. 35 (m, 1H), 3.18- 3.06 (m, 4H), 2.51-2. 40 (m, 1H), 2.39-2. 26 (m, 2H), 1.11 (t, J= 7.1 Hz, 3H).
 

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