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Chemical Structure| 149107-92-6 Chemical Structure| 149107-92-6

Structure of 149107-92-6

Chemical Structure| 149107-92-6

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Product Details of [ 149107-92-6 ]

CAS No. :149107-92-6
Formula : C20H21NO4
M.W : 339.39
SMILES Code : O=C1N(C(C2=CC=CC=C2)=O)[C@@H](C3=CC=CC=C3)[C@H]1OC(C)(OC)C
MDL No. :MFCD09750989

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Application In Synthesis of [ 149107-92-6 ]

* 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 [ 149107-92-6 ]

[ 149107-92-6 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 149107-92-6 ]
  • [ 10482-56-1 ]
  • α-terpeneyl N-benzoyl-(2'R,3'S)-phenylisoserine ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% To a solution of (-)-menthol (22 mg, 0.143 mmol) in 1 mL of THF at -45 C was added dropwise 0.143 mL of a 1.0 M solution of lithium hexamethyldisilazide in THF. After 1 h at -45 C, a solution of (+)-cis-1-benzoyl-3-(2-methoxy-2-propyloxy)-4-phenylazetidin-2-one (58 mg, 0.172 mmol) in 1 mL of THF was added dropwise to the mixture. The solution was warmed to 0 C and kept at that temperature for 2 h before 1 mL of a 10% solution of AcOH in THF was added. The mixture was partitioned between saturated aqueous NaHCO3 and 60/40 ethyl acetate/hexane. Evaporation of the organic layer gave 73 mg of a residue which was dissolved in 6 mL of THF at 0 C. To this solution was added 0.9 mL of glacial acetic acid and 0.9 mL of water. The mixture was stirred at 0 C for 3 h, then partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. Evaporation of the ethyl acetate solution gave 70 mg of material which was purified by chromatography on silica gel to give 48 mg (80%) of a-terpineyl N-benzoyl-(2'R,3'S)-phenylisoserine ester.
 

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