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Chemical Structure| 58644-53-4 Chemical Structure| 58644-53-4

Structure of 58644-53-4

Chemical Structure| 58644-53-4

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Product Citations

Product Citations

Wang, Feijun ; Frankowski, Kevin J. ;

Abstract: We developed an electrochemical carboamidation sequence that affords either cyclic β-amidoamine products via direct functionalization or linear hydroxybisamide products via a ring opening pathway. The reaction pathway was dependent on the nature of the N-acyl activating group, with carbamate groups favoring direct isocyanide addition to the N-acyliminium ion intermediate and the benzoyl activating group favoring the ring opening–functionalization pathway. Both protocols are one-pot reaction sequences, have general applicability, and lead to peptide-like products of greatly increased molecular complexity.

Alternative Products

Product Details of [ 58644-53-4 ]

CAS No. :58644-53-4
Formula : C4H5N
M.W : 67.09
SMILES Code : [C-]#[N+]C1CC1
MDL No. :MFCD04117501

Safety of [ 58644-53-4 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H225-H301-H311-H315-H319-H331-H335
Precautionary Statements:P210-P261-P280-P301+P310-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P311
Class:6.1(3)
UN#:2929
Packing Group:

Application In Synthesis of [ 58644-53-4 ]

* 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 [ 58644-53-4 ]

[ 58644-53-4 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 58644-53-4 ]
  • [ 107259-06-3 ]
  • [ 64-19-7 ]
  • acetic acid (1-tert-butoxycarbonylaminocyclopropyl)cyclopropylcarbamoyl methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; To a solution of (l-formylcyclopropyl)carbamic acid tert-butyl ester (393 mg, 2.12 mmol) in CH2Cl2 (4 mL) was added acetic acid (191 mg, 0.182 mL, 3.18 mmol), and cyclopropyl isocyanide (142 mg, 2.12 mmol). The reaction mixture was stirred overnight at room temperature and then concentrated under reduced pressure to yield crude acetic acid (1- tert-butoxycarbonylaminocyclopropyl)cyclopropylcarbamoyl methyl ester which was used in the next step without further purification.
  • 2
  • [ 58644-53-4 ]
  • [ 107259-06-3 ]
  • [ 64-19-7 ]
  • acetic acid (1-tert-butoxycarbonylaminocyclopropyl)cyclopropyl-carbamoyl-methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; Step 6; [0202] To a solution of (l-formylcyclopropyl)carbamic acid tert-butyl ester (393 mg, 2.12 mmol) in CH2Cl2 (4 niL) was added acetic acid (191 mg, 0.182 mL, 3.18 mmol), and cyclopropyl isocyanide (142 mg, 2.12 mmol). The reaction mixture was stirred overnight at room temperature and then concentrated under reduced pressure to yield crude acetic acid (1- tert-butoxycarbonylammocyclopropyi)cyclopropylcarbamoyl methyl ester which was used in the next step without further purification
 

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