L-Valine, N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxobutyl)-, methyl ester synthesis

3synthesis methods

Product Name:L-Valine, N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxobutyl)-, methyl ester
CAS Number:934736-45-5
Molecular formula:C24H28N2O3
Molecular Weight:392.49

N-[(2'-Cyano[1,1'-biphenyl]-4-yl)methyl]-L-valine methyl ester

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L-Valine, N-[(2'-cyano[1,1'-biphenyl]-4-yl)methyl]-N-(1-oxobutyl)-, methyl ester

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Yield:934736-45-5 74.9%

Reaction Conditions:

with dmap;triethylamine in dichloromethane at 20 - 45;Inert atmosphere;

Steps:

4.7. N-Butyryl-N-((2'-cyanobiphenyl-4-yl)methyl)-l-Valine methyl ester (6b)

To 31 mL of dichloromethane was added methyl ester 5b (3.97 g, 11.8 mmol), TEA (5 mL, 39.10 mmol) and DMAP (0.09 g, 0.7 mmol). To the mixture was added dropwise carbonyl chloride (2.1 mL, 35.60 mmol) under nitrogen. After stirring for 1 h, the temperature was raised to 45 °C, and the mixture was monitored by TLC till completion. To the mixture was added 10 mL of 1 M dilute aqueous hydrochloride. The organic phase was separated, washed with saturated NaHCO₃ solution, and dried over MgSO₄. After filtration, the solvent was removed under reduced pressure, and the residue was purified by flash column chromatograph to afford a colorless oil. Yield 74.9%. ¹H NMR (CDCl₃, 300 MHz) δ: 7.72-7.26 (8H, m, Ph-H), 5.08 (d, J = 15.6 Hz), 5.00 (1H, d, J = 10.5 Hz, -CO-CH-N-), 4.68 (d, J = 17.9 Hz), 4.26 (d, J = 15.6 Hz), 4.04 (2H, d, J = 10.8 Hz, -N-CH₂-), 3.43 (s), 3.35 (3H, s, -OCH₃), 2.43-2.30 (3H, m, -CO-CH₂-, -CHCH₃), 1.28-0.84 (9H, m,); ¹³C NMR (CDCl₃, 125 MHz) δ: 178.2, 175.0, 145.1, 141.1, 139.9, 138.3, 137.5, 130.6, 130.6, 130.1, 130.1, 129.2, 129.2, 121.5, 116.4, 66.8, 55.8, 55.4, 39.3, 30.2, 21.1, 20.9, 20.9, 18.6. ESI-MS (m/z): 379.2[M+1]⁺, 401.2[M+Na]⁺; HR-MS: 378.1944, C₂₃H₂₆N₂O₃.

References:

Nie, Yong-Yan;Da, Ya-Jing;Zheng, Hao;Yang, Xiao-Xia;Jia, Lin;Wen, Cai-Hong;Liang, Li-Sha;Tian, Juan;Chen, Zhi-Long [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 8,p. 2747 - 2761] Location in patent:experimental part

72-18-4 Synthesis

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