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Chemical Structure| 1197-17-7 Chemical Structure| 1197-17-7
Chemical Structure| 1197-17-7

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Product Details of Tranexamic acid impurity B

CAS No. :1197-17-7
Formula : C8H15NO2
M.W : 157.21
SMILES Code : O=C([C@H]1CC[C@@H](CN)CC1)O
MDL No. :MFCD19706018
InChI Key :GYDJEQRTZSCIOI-UHFFFAOYSA-N
Pubchem ID :5526

Safety of Tranexamic acid impurity B

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

Application In Synthesis of Tranexamic acid impurity B

* 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.

  • Upstream synthesis route of [ 1197-17-7 ]
  • Downstream synthetic route of [ 1197-17-7 ]

[ 1197-17-7 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 1197-17-7 ]
  • [ 28920-43-6 ]
  • [ 188715-40-4 ]
YieldReaction ConditionsOperation in experiment
83%
Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃; for 2.5 h;
Stage #2: With hydrogenchloride In 1,4-dioxane; water
Step 1: Dissolve 4-Aminomethyl-cyclohexanecarboxylic acid ((39); 1.15g, 7.30mmol) in 1,4-dioxane (12.0mL) and 10percent aqu. Na2CO3 (23.2mL) and add Fmoc-Cl (2.26g, 8.76mmol). Stir the reaction mixture for 2.5h at rt. Add 1M aqu HCl (42.0mL) to the mixture and extract with EtOAc (3 times). Wash the combined organic layers with 1M aqu HCl, water and brine, extract the combined aqu layers once again with EtOAc, dry the combined organic layers with Na2SO4 and remove solvent under reduced pressure. The left crude product is washed with ice cold EtOAc and dried in oil pump vacuum to obtain (40) as a white solid (2.28g, 83percent). No further purification. [M. Nichifor; E. H. Schacht; Tetrahedron;1994; 50; 12; 3747-3760]. 1H NMR (400MHz, CDCl3): 0.87-1.02 (br.m, 2 H); 1.34-1.52 (br.m, 4 H); 1.81 (br.d, 2 H, J 6Hz); 1.90-2.11 (br.s, 1 H); 2.12-2.35 (br.m, 1 H); 3.03 (Ψt, 2 H, J = 6.2Hz); 4.19 (br.Ψt, 1 H, J = 6.5Hz); 4.42 (br.Ψd, 2 H, J = 6.5Hz); 4.74 (br.s, 1 H); 7.30 (Ψt, 2 H, J = 7.4Hz); 7.38 (Ψt, 2 H, J = 7.4Hz); 7.57 (d, 2 H, J = 7.4Hz); 7.75 (d, 2 H, J = 7.4Hz).
References: [1] Patent: EP1577289, 2005, A1, . Location in patent: Page/Page column 23.
[2] Organic Letters, 2008, vol. 10, # 10, p. 1881 - 1884.
  • 2
  • [ 1197-17-7 ]
  • [ 82911-69-1 ]
  • [ 188715-40-4 ]
References: [1] Patent: US2004/14763, 2004, A1, . Location in patent: Page 17; 18.
 

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