ChemicalBook CAS DataBase List N-Trityl Losartan Carboxaldehyde

N-Trityl Losartan Carboxaldehyde synthesis

11synthesis methods

Product Name:N-Trityl Losartan Carboxaldehyde
CAS Number:133910-00-6
Molecular formula:C41H35ClN6O
Molecular Weight:663.21

76-83-5 Synthesis

76-83-5
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114798-36-6 Synthesis

114798-36-6
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133910-00-6
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Yield:133910-00-6 88%

Reaction Conditions:

with trimethylamine in dichloromethane at 20; for 5 h;

Steps:

3.9 6.1.3.9 2-Butyl-5-chloro-3-[2'-(2-trityl-2H-tetrazol-5-yl)biphenyl-4-ylmethyl]-3H-imidazole-4-carbaldehyde (9) [42]

To a solution of 8 (1.02g, 2.43mmol) in anhydrous CH₂Cl₂ (10mL) were added trimethylamine (373μL, 2.68mmol) and trityle chloride (747mg, 2.68mmol). The mixture was stirred at room temperature for 5h. EtOAc (60mL) was added and the resulting solution was washed with water (4×30mL), dried (MgSO₄) and the solvent was removed under vacuum to give a residue which was purified by column chromatography (eluent: cyclohexane/EtOAc, 85:15) to give 1.41g (2.13mmol, 88% yield) of white solid. M. p. 86-89°C. ¹H NMR (250MHz, DMSO-d₆): δ 0.81 (t, J=7.3Hz, 3H, CH₃), 1.18-1.33 (m, 2H, CH₂), 1.43-1.57 (m, 2H, CH₂), 2.60-2.66 (m, 2H, CH₂), 5.58 (s, 2H, CH₂N), 7.01-7.09 (m, 4H, H_arom), 7.50-7.70 (m, 4H, H_arom), 9.68 (s, 1H, CHO).

References:

Meyer, Maxime;Foulquier, Sébastien;Dupuis, Fran?ois;Flament, Stéphane;Grimaud, Linda;Henrion, Daniel;Lartaud, Isabelle;Monard, Gérald;Grillier-Vuissoz, Isabelle;Boisbrun, Michel [European Journal of Medicinal Chemistry,2018,vol. 158,p. 334 - 352]

83857-96-9 Synthesis