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Chemical Structure| 144256-11-1 Chemical Structure| 144256-11-1

Structure of 144256-11-1

Chemical Structure| 144256-11-1

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Product Details of [ 144256-11-1 ]

CAS No. :144256-11-1
Formula : C15H20O5
M.W : 280.32
SMILES Code : O=C(OC[C@H]1OC(C)(C)OC1)CCC2=CC=C(O)C=C2
MDL No. :MFCD11045071

Safety of [ 144256-11-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 144256-11-1 ]

* 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 [ 144256-11-1 ]

[ 144256-11-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 154467-16-0 ]
  • [ 144256-11-1 ]
  • [ 106-89-8 ]
  • [ 144481-98-1 ]
YieldReaction ConditionsOperation in experiment
49.7% Example 7 Landiolol hydrochloride (2) from (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate (3) A suspension of (R,R)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-ciclohexanediamino cobalt (16) (47 mg, 0.0780 mmol) in dichloromethane (1 ml) is added with 4-nitrobenzoic acid 17 (27 mg, 0.156 mmol). The mixture is left under stirring for 45' at 20-25C until a dark color appears. The resulting solution is concentrated to a volume of about 0.5 ml, added with 0.5 ml of MTBE, concentrated to a volume of 0.5 ml and finally added with 0.5 ml of MTBE, then with (S)-(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 3-(4-hydroxyphenyl)propanoate (3), (0.5 g, 1,77 mmol) and then with epichlorohydrin (compound of formula 4 in which X is chlorine) (0.37 g, 3,89 mmol). The mixture is left under stirring at 20-25C, monitoring by UPLC. After completion of the reaction, toluene (10 ml) and water (10 ml) are added and the phases are separated. The organic phase is evaporated recovering the enriched (S)-epichlorohydrin, then added again with toluene (10 ml) and washed with 10% NaOH (10 ml). The resulting solution is concentrated to a volume of about 2 ml, added with 5 ml of acetonitrile, concentrated to a volume of 2 ml and finally added with 10 ml of acetonitrile). The suspension is filtered thus recovering the catalyst and the solution is added with potassium carbonate 0.79 g (5,64 mmol), and KI 0.026 g (0.161 mmol), refluxed for 2 h, then added with 2-(morpholine-4-carboxamido)ethanamino oxalate (6) (1.07 g, 4.03 mmol). The mixture is refluxed under stirring, monitoring by UPLC. After completion of the reaction, ethyl acetate (20.0 ml) and water (20 ml) are added and the phases are separated. The organic phase is then adjusted to pH 4-5 with hydrochloric acid and extracted with water (20 ml). The phases are separated and the resulting aqueous phase is then adjusted to pH 11-12 with sodium hydroxide and re-extracted with ethyl acetate (20 ml). The resulting solution is concentrated to a volume of about 5 ml, added with 20 ml of isopropanol, concentrated to a volume of 5 ml and finally added with 30 ml of isopropanol, then 18% isopropanol hydrochloric acid (0.24 g, 1.18 mmol). The solvent is then evaporated off under reduced pressure and the residue is crystallized from acetone (10 ml). The suspension is filtered and the crystal is dried at 25C for 12 h to obtain 0.48 g (49.7% total, enantiomeric purity: 99.8%) of a white solid. m.p.: 126C (from literature 123-127C) LC-MS (ESI+) [M+H]+ = 510 FT-IR (UATR, cm-1): 3265, 2941, 2789, 2419, 1723, 1615, 1538, 1515, 1435, 1371, 1260. 1242, 1196, 1118, 1047, 887, 838, 821, 771.
 

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