Trityl Valsartan synthesis

3synthesis methods

Product Name:Trityl Valsartan
CAS Number:783369-52-8
Molecular formula:C43H43N5O3
Molecular Weight:677.83

N-[(2′-(1-Triphenylmethyl-Tetrazole-5-Yl)Biphenyl-4-Yl]-Methyl]-N-Valeryl-L- Valine Benzyl Ester

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Yield:783369-52-8 86%

Reaction Conditions:

with hydrogen;5%-palladium/activated carbon in ethyl acetate at 20; for 3 h;

Steps:

28

A mixture of benzyl N-pentanoyl-N-[{2'-[1-(triphenylmethyl)-1 H-tetrazol-5-yl]- 1 ,1'-biphenyl-4-yl}methyl]-L-valinate (0.3 g) in AcOEt (3 ml_) containing 5% palladium on activated Charcoal (Pd/C, 34 mg ) was hydrogenated at room temperature for 3h. The resulting crude product was filtered through a Celite pad and the solvent was evaporated to dryness to furnish the desired product (0.23 g, 86%). ¹H-NMR (400 MHz, CDCI₃): δ 0.85 and 0.98 (2 d, 3 H each, J = 6.8 Hz, 2 CH₃ (iPr)), 0.88 (t, 3 H, J = 7.2 Hz, CH₃ (pentanoyl)), 1.29 (m, 2 H, CH₂Me), 1.61 (m, 2 H, CH₂Et), 2.36 (m, 2 H, CH₂CO), 2.74 (m, 1 H, CH(iPr)), 3.51 (d, 1 H, J = 10.8 Hz, CHN), 4.28 and 4.60 (2 d, 1 H each, J = 16.2 Hz, CH₂-N), 6.94-7.92 (m, 23 H, H-Ar) ppm. ¹³C-NMR (100 MHz, CDCI₃): δ 13.8, EPO 19.5 and 19.7 (CH₃), 22.3 (CH₂), 27.0 (CH₂), 27.1 (CH), 34.1 (CH₂), 54.8 (CH₂), 72.6 (CH), 82.8 (C), 126.1-141.3 (CH- and C-ipso-Ar), 164.0 (CN), 171.4 and 177.3 (CO) ppm. IR (υ): 2960 (broad band, OH), 1741 (CO-acid), 1610 (CO-amide) cm^"1. Mp 170 ⁰C.

References:

WO2006/67216,2006,A2 Location in patent:Page/Page column 27-28

72-18-4 Synthesis

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References

124750-51-2 Synthesis

5-(4'-Bromomethyl-1,1'-biphenyl-2-yl)-1-triphenylmethyl-1H-tetrazole

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References